Skip to main content
SpringerLink
Log in

The Quinazoline Alkaloids

  • Chapter
Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Abstract

Quinazoline (1) is a building block for approximately eighty naturally occurring alkaloids isolated from a number of families of the plant kingdom, from microorganisms and from animals. The first known quinazoline alkaloid was vasicine (peganine), isolated in 1888 from Adhatoda vasica, and later from other species. This plant has been used in Indian indigenous medicine for centuries. The antimalarial activity of febrifugine (9) provided a strong stimulus for the synthesis and biological screening of a vast number of quinazoline derivatives. A number of interesting new alkaloids have been discovered in a variety of sources, and study of the chemistry and pharmacology of quinazoline alkaloids has intensified in the last twenty years. In many cases, structures of the quinazolines have been confirmed by synthesis. The biosynthesis of this type of alkaloid has received intensive study also.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 16.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Ablondi, F., S. Gordon, J. Morton II, and J. H. Williams: An Antimalarial Alkaloid from Hydrangea. II. Isolation. J. Org. Chem. 17, 14 (1952).

    CAS  Google Scholar 

  2. Amin, A. H., and D. R. Mehta: A Bronchodilator Alkaloid (Vasicinone) from Adhatoda vasica Nees. Nature 184, 1317 (1959).

    CAS  Google Scholar 

  3. Amin, A. H., D. R. Mehta, and S. S. Samarth: Biological Activity in the Quinazolone Series. Progr. Drug Res. 14, 218 (1970).

    Google Scholar 

  4. Arif, A. J., Ch. Singh, A. P. Bhaduri, C. M. Gupta, A. W. Khan, and M. M. Dhar: Actinomycetes Studies: Part II — Cell-free Synthesis of Echinomycin & an Echinomycin Analogue. Indian J. Biochem. 7, 193 (1970).

    CAS  Google Scholar 

  5. Armarego, W. L. F.: Quinazolines. Adv. Heterocyclic Chem. 24, 1 (1979).

    CAS  Google Scholar 

  6. Armarego, W. L. F.: In: The Chemistry of Heterocyclic Compounds Vol. 24/1: Quinazolines. New York- London-Sydney: Interscience Publishers Ltd. 1967.

    Google Scholar 

  7. Armarego, W. L. F., and Ph. A. Reece: Quinazolines. Part XXI. Synthesis of cis-2-Amino-8a-carboxymethyl-3,4,4a,5,6,7,8,8a-octahydroquinazoline and Related Compounds. Conversions of Perhydroquinazolin-2-ones into 2-Amino-3,4,4a,5,6,7,8,8a- octahydroquinazolines. J. Chem. Soc. Perkin Trans. I 1975, 1470.

    Google Scholar 

  8. Armarego, W. L. F., and P. G. Tucker: Quinazolines. XXIV. TJje Synthesis of 2,4- Diazatetracyclo[7,3,l,l7,11,O1,6]tetradecanes (Adamantano[l,2-d]pyrimidines). Aust. J. Chem. 32, 1805 (1979), and earlier papers.

    Google Scholar 

  9. Arndt, R.. R., S. H. Eggers, and A. Jordaan: The Alkaloids of Anisotes sessiliflorus C.B.C1. (Acanthaceae) — Five New 4-Quinazolone Alkaloids. Tetrahedron 23, 3521 (1967).

    CAS  Google Scholar 

  10. Asahina, Y., and K. Kashiwaki: Chemical Constituents of the Fruits of Evodia rutaecarpa. J. Pharm. Soc. Japan No. 405, 1293 (1915).

    Google Scholar 

  11. Asahina, Y., and T. Ohta: Eine Synthese des Evodiamins. Ber. dtsch. Chem. Ges. 61, 319; 869 (1928).

    Google Scholar 

  12. Atal, C. K.: Chemistry and Pharmacology of Vasicine — A New Oxytocic and Abortifacient. New Delhi: Ray Bandhu Industrial Co. 1980.

    Google Scholar 

  13. Ayafor, J. F., B. L. Sondengam, and B. T. Ngadjui: Quinoline and Indolopyridoquinazoline Alkaloids from Vepris louisii. Phytochemistry 21, 2733 (1982).

    CAS  Google Scholar 

  14. Baker, B. R., F. J. Mc Evoy, R. E. Schaub, J. P. Joseph, and J. H. Williams: An Antimalarial Alkaloid from Hydrangea. XXI. Synthesis and Structure of Febrifugine and Isofebrifugine. J. Org. Chem. 18, 178 (1953).

    CAS  Google Scholar 

  15. Baker, B. R., and F. J. Mc Evoy: An Antimalarial Alkaloid from Hydrangea. XXIII. Synthesis by the Pyridine Approach. II. J. Org. Chem. 20, 136 (1955).

    CAS  Google Scholar 

  16. Barringer Jr., D. F., G. Berkelhammer, S. D. Carter, L. Goldman, and A. E. Lanzilotti: The Stereochemistry of Febrifugine. I. The Equilibrium between cis- and trans-(3-Substituted 2-piperidyl)-2-propanones. J. Org. Chem. 38, 1933 (1973).

    CAS  Google Scholar 

  17. Barringer Jr., D. F., G. Berkelhammer, and R. S. Wayne: The Stereochemistry of Febrifugine. II. Evidence for the Trans Configuration in the Piperidine Ring. J. Org. Chem. 38, 1937 (1973).

    CAS  Google Scholar 

  18. Batsuren, D., M. V. Telezhenetskaya, S. Yu. Yunusov, and T. Baldan: Alkaloids of Peganum nigellastrum. Khim. Prir. Soedin. 1978, 418 (Russ).

    Google Scholar 

  19. Bergman, J.: The Quinazolinocarboline Alkaloids. In: (133); Vol. XXI, p. 30 (1983).

    Google Scholar 

  20. Bergman, J., and S. Bergman: Synthesis of Rutaecarpine and Related Indole Alkaloids. Heterocycles 16, 347 (1981).

    CAS  Google Scholar 

  21. Bergman, J., B. Egestad, and J.-O. Lindström: The Structure of Some Indolic Constituents in Couroupita guaianensis Aubl. Tetrahedron Lett. 1977, 2625.

    Google Scholar 

  22. Bhatnagar, A. K., S. Bhattacharji, and S. P. Popli: On the Identity of Vasicinol. Indian J. Chem. 3, 525 (1965).

    Google Scholar 

  23. Bhatnagar, A. K., and S. P. Popli: Mass Fragmentation of the Alkaloids of Adhatoda vasica Nees. Indian J. Chem. 4, 291 (1966).

    CAS  Google Scholar 

  24. Bhattacharyya, J., and S. C. Pakrashi: Carbon-13 NMR Analysis of Some 4-Quinazolinone Alkaloids and Related Compounds. Heterocycles 14, 1469 (1980).

    CAS  Google Scholar 

  25. Bhattacharyya, J., and S. C. Pakrashi: The Identity of Glycophymine and Glycosminine: an Alkaloid of Glycosmis arborea (Roxb.) DC. Heterocycles 12, 929 (1979).

    CAS  Google Scholar 

  26. Bhattacharyya, P., M. Sakar, T. Roychowdhury, and D. P. Chakraborty: New Synthesis of the Quinazolone Alkaloids Arborine and Glycorine. Chem. and Ind. 1978, 532.

    Google Scholar 

  27. Bird, C. W.: The Structure of Methylisatoid. Tetrahedron 19, 901 (1963).

    CAS  Google Scholar 

  28. Borr, H. G.: Chinazolin-Alkaloide. In: Fortschritte der Alkaloid-Chemie seit 1933, p. 331, Berlin: Akademie-Verlag 1950; Ergebnisse der Alkaloid-Chemie bis 1960, p. 741, Berlin: Akademie-Verlag 1961.

    Google Scholar 

  29. Bowen, I. H., K. P. W. C. Perera, and J. R. Lewis: Alkaloids of the Leaves of Glycosmis bilocularis. Phytochemistry 17, 2125 (1978).

    Google Scholar 

  30. Brufani, M., W. Fedeli, F. Mazza, A. Gerhard, and W. Keller-Schierlein: The Structure of Tryptanthrin. Experientia 27, 1249 (1971).

    CAS  Google Scholar 

  31. Buděšinsky, Z., P. Lederer, and J. Danek: 3-(3-Amino-2-hydroxypropyl)- and 3-(3- Aminoacetoxy)-4(3H)-quinazolines. Collect. Czech. Chem. Comm. 42, 3473 (1977).

    Google Scholar 

  32. Budzikiewicz, H., C. Djerassi, and D. H. Williams: Structure Elucidation of Natural Products by Mass Spectrometry, VoL I, p. 212. San Francisco: Holden-Day, Inc. 1964.

    Google Scholar 

  33. Büchi, G., P. R. De Shong, S. Katsumura, and Y. Sugimura: Total Synthesis of Tryptoquivaline G. J. Amer. Chem. Soc. 101, 5084 (1979).

    Google Scholar 

  34. Büchi, G., K. Ch. Luk, B. Kolbe, and J. M. Townsend: Four New Mycotoxins of Aspergillus clavatus Related to Tryptoquivaline. J. Org. Chem. 42, 244 (1977).

    Google Scholar 

  35. Cambridge, G. W., A. B. A. Jansen, and D. A. Jarman: Bronchodilating Action of Vasicinone and Related Compounds. Nature 196, 1217 (1962).

    CAS  Google Scholar 

  36. Canonica, L., B. Danieli, P. Manitto, and G. Russo: New Quinazolinocarboline Alkaloids from Euxylophora paraensis Hub. Tetrahedron Lett. 1968, 4865.

    Google Scholar 

  37. Chakravarti, D., and R. N. Chakravarti: Quinazolone Alkaloids. J. Proc. Inst. Chemists (India) 39 (Part III), 131 (1967).

    CAS  Google Scholar 

  38. Chakravarti, D., R. N. Chakravarti, L. A. Cohen, B. Das Gupta, S. Dutta, and H. K. Miller: Alkaloids of Glycosmis arborea — II. Structure of Arborine. Tetrahedron 16, 224 (1961).

    CAS  Google Scholar 

  39. Chakravarti, D., R. N. Chakravarti, and S. C. Chakravarti: Arborine and Glycosine. Science and Culture (India) 18, 553 (1953).

    CAS  Google Scholar 

  40. Chakravarti, D., R. N. Chakravarti, and S. C. Chakravarti: Alkaloids of Glycosmis arborea. Part I. Isolation of Arborine and Arborinine: The Structure of Arborine. J. Chem. Soc. 1953, 3337.

    Google Scholar 

  41. Chakravarti, R. N.: Chemistry of Arborine. Bull. Calcutta School Trop. Med. 11, 37 (1963).

    CAS  Google Scholar 

  42. Chakravarti, R. N., and S. C. Chakravarti: Chemical Investigation of Glycosmis arborea Correa. J. Proc. Inst. Chemists (India) 24, 96 (1952).

    CAS  Google Scholar 

  43. Chatterjee, A., S. Bose, and C. Ghosh: Rhetsine and Rhetsinine: The Quinazoline Alkaloids of Xanthoxylum rhetsa. Tetrahedron 7, 257 (1959).

    CAS  Google Scholar 

  44. Chatterjee, A., and J. Mitra: Chemistry of Rhetine and Synthesis of Rhetsine. The Alkaloids of Zanthoxylum rhetsa. Science and Culture (India) 25, 493 (1960).

    CAS  Google Scholar 

  45. Chatterjee, A., and M. Ganguly: Alkaloidal Constituents of Peganum harmala and Synthesis of the Minor Alkaloid Deoxyvasicinone. Phytochemistry 7, 307 (1968).

    CAS  Google Scholar 

  46. Chatterjee, A., and S. Ghosh Majumdar: Alkaloids of Glycosmispentaphylla (Retz.) DC. Part I. J. Amer. Chem. Soc. 76, 2459 (1954).

    CAS  Google Scholar 

  47. Chatterjee, A., and S. Ghosh Majumdar: Constitution and Synthesis of Glycosin, the New Alkaloid of Glycosmis pentaphylla Retz. DC. J. Amer. Chem. Soc. 75, 4365 (1953).

    CAS  Google Scholar 

  48. Chatterjee, M. L., and M. S. DE: Pharmacological Studies with Arborine. Bull. Calcutta School Trop. Med. 8, 102 (1960).

    CAS  Google Scholar 

  49. Chien, P.-L., and C. C. Cheng: Structural Modification of Febrifugine. Some Methylenedioxy Analogs. J. Med. Chem. 13, 867 (1970).

    CAS  Google Scholar 

  50. Chou, T. Q., F. Y. Fu, and Y. S. Kao: Antimalarial Constituents of Chinese Drug, Ch’ang Shan, Dichroa febrifuga Lour. J. Amer. Chem. Soc. 70, 1765 (1948).

    CAS  Google Scholar 

  51. Clardy, I., J. P. Springer, G. Büchi, K. Matsuo, and R. Wightman: Tryptoquivaline and Tryptoquivalone, Two Tremorgenic Metabolites of Aspergillus clavatus. J. Amer. Chem. Soc. 97, 663 (1975).

    CAS  Google Scholar 

  52. Culbertson, H., J. C. Decius, and B. E. Christensen: Quinazolines. XIII. A Study of the Infrared Spectra of Certain Quinazoline Derivatives. J. Amer. Chem. Soc. 74, 4834 (1952).

    CAS  Google Scholar 

  53. Danieli, B., C. Farachi, and G. Palmisano: A New Indolopyridoquinazoline in the Bark of Euxylophora paraensis. Phytochemistry 15, 1095 (1976).

    CAS  Google Scholar 

  54. Danieli, B., G. Lesma, and G. Palmisano: A New Tryptophan Derived Alkaloid from Evodia rutaecarpa (Juss.) Benth. et Hook. Experientia 35, 156 (1979).

    CAS  Google Scholar 

  55. Danieli, B., G. Lesma, and G. Palmisano: Quinazolinocarboline Alkaloids Chemistry: Reactivity of Euxylophorines—Part I. Heterocycles 12, 353 (1979).

    CAS  Google Scholar 

  56. Danieli, B., G. Lesma, and G. Palmisano: The Configuration of (+)-Evodiamine: a Long-standing Problem in the Chemistry of Indole Alkaloids. J. Chem. Soc. Chem. Commun. 1982, 1092.

    Google Scholar 

  57. Danieli, B., P. Manitto, F. Ronchetti, and G. Russo: New Indolopyridoquinazoline Alkaloids from Euxylophora paraensis. Phytochemistry 11, 1833 (1972).

    CAS  Google Scholar 

  58. Danieli, B., P. Manitto, F. Ronchetti, G. Russo, and G. Ferrari: Paraensine, a New Indolopyridoquinazoline Alkaloid from Euxylophora paraensis Hub. Experientia 28, 249 (1972).

    CAS  Google Scholar 

  59. Danieli, B., and G. Palmisano: A New Approach to Quinazolinocarboline Alkaloids: Synthesis of (±)-Evodiamine, Rutaecarpine and Dehydroevodiamine. Heterocycles 9, 803 (1978).

    CAS  Google Scholar 

  60. Danieli, B., and G. Palmisano: Unusually Simple Methylation at N-13 of Indolo-pyridoquinazoline Alkaloids. Gazz. Chim. Ital. 105, 45 (1975).

    CAS  Google Scholar 

  61. Danieli, B., G. Palmisano, G. Rainoldi, and G. Russo: 1-Hydroxyrutaecarpine from Euxylophora paraensis. Phytochemistry 13, 1603 (1974).

    CAS  Google Scholar 

  62. Danieli, B., G. Palmisano, G. Russo, and G. Ferrari: Minor Indolopyridoquinazoline Alkaloids from Euxylophora paraensis. Phytochemistry 12, 2521 (1973).

    CAS  Google Scholar 

  63. Danieli, B., and G. Palmisano: Ind-N-Alkylation of Rutecarpine and Synthesis of Two Novel Related Heterocyclic Ring Systems: Indolo[l′,2′:3,4]pyrazo[l,2-a]quinazoline and Indolo[l′,2′:3,4][l,4]diazepino[l,2-a]quinazoline. J. Heterocycl. Chem. 14, 839 (1977).

    CAS  Google Scholar 

  64. Danieli, B., G. Lesma, and G. Palmisano: Quinazolinocarboline Alkaloids Chemistry: Thermal Rearrangement of 14-Alkylindolo[2′,3′:3,4]pyrido[2,1-b]quinazolin-5-one. Part II. Heterocycles 12, 1433 (1979).

    CAS  Google Scholar 

  65. De Corrêa, D. B., O. R. Gottlieb, and A. P. De Padua: Chemistry of Brazilian Rutaceae. I. Dihydrocinnamic Acids from Hortia badinii. Phytochemistry 14, 2059 (1975).

    Google Scholar 

  66. De Corrêa, D. B., O. R. Gottlieb, A. P. De Padua, and A. I. Da Rocha: The Chemistry of Brazilian Rutaceae. II. Constituents of Hortia longifolia. Rev. Latinoamer. Quirn. 7 (1), 43 (1976) [Chem. Abstr. 84, 161790g (1976)].

    Google Scholar 

  67. Devi, G., R. S. Kapil, and S. P. Popli: Potential CNS & CVS Agents: Syntheses Based on Vasicinone. Indian J. Chem. 14B, 354 (1976).

    Google Scholar 

  68. Dhar, K. L., M. P. Jain, S. K. Koul, and C. K. Atal: Vasicol, a New Alkaloid from Adhatoda vasica. Phytochemistry 20, 319 (1981).

    CAS  Google Scholar 

  69. Dhar, M. M., Ch. Singh, A. W. Khan, A. J. Arif, C. M. Gupta, and A. P. Bhaduri: Cell-free Synthesis of Echinomycin and an Echinomycin Analog. Pure Appl. Chem. 28, 469 (1971).

    CAS  Google Scholar 

  70. Döpke, W.: Ergebnisse der Alkaloid-Chemie 1960–1968. 2 Bände. Berlin: Akademie-Verlag. 1976/1978.

    Google Scholar 

  71. Donovan, D. G. O., and H. Horan: The Biosynthesis of Arborine. J. Chem. Soc. (C) 1970, 2466.

    Google Scholar 

  72. Dreyer, D. L., and R. C. Brenner: Alkaloids of Some Mexican Zanthoxylum Species. Phytochemistry 19, 935 (1980).

    CAS  Google Scholar 

  73. Elguero, J., C. Marzin, A. R. Katritzky, and P. Linda: In: The Tautomerism of Heterocycles. Advances in Heterocyclic Chemistry (A. R. Katritzky and A. J. Boulton, ed.), Suppl. 1, p. 129. New York-San Francisco-London: Academic Press. 1976.

    Google Scholar 

  74. Fedeli, W., and F. Mazza: Crystal Structure of Tryptanthrin (Indolo[2,l- b]quinazoline-6,12-dione). J. Chem. Soc. Perkin Trans. II 1974, 1621.

    Google Scholar 

  75. Fiedler, E., H. P. Fiedler, A. Gerhard, W. Keller-Schierlein, W. A. König, and H. Zähner: Stoffwechselprodukte von Mikroorganismen. 156. Mitteilung. Synthese und Biosynthese substituierter Tryptanthrine. Arch. Mikrobiol. 107, 249 (1976).

    CAS  Google Scholar 

  76. Fish, F., I. A. Meshal, and P. G. Waterman: Minor Alkaloids of Araliopsis tabouensis. Planta Med. 29, 310 (1976).

    CAS  Google Scholar 

  77. Fishman, M., and Ph. A. Cruickshank: Febrifugine Antimalarial Agents. I. Pyridine Analogs of Febrifugine. J. Med. Chem. 13, 155 (1970).

    CAS  Google Scholar 

  78. Fitzgerald, J. S., S. R. Johns, J. A. Lamberton, and A. H. Redcliffe: 6,7,8,9- Tetrahydropyridoquinazolines, a New Class of Alkaloids from Mackinlaya Species (Araliaceae). Aust. J. Chem. 19, 151 (1966).

    CAS  Google Scholar 

  79. Friedländer, P., and W. Roschdestwensky: Über ein Oxydationsprodukt des Indigblaues. Ber. dtsch. Chem. Ges. 48, 1841 (1915).

    Google Scholar 

  80. Ghosal, S., R. B. P. S. Chauhan, and R. Mehta: Alkaloids of Sida cordifolia. Phytochemistry 14, 830 (1975).

    Google Scholar 

  81. Gopinath, K. W., T. R. Govindachari, and U. Ramadas Rao: The Alkaloids of Zanthoxylum rhetsa DC. Tetrahedron 8, 293 (1960).

    CAS  Google Scholar 

  82. Goto, T., Y. Kishi, S. Takahashi, and Y. Hirata: Tetrodotoxin. Tetrahedron 21, 2059 (1965), and references cited therein.

    CAS  Google Scholar 

  83. Gröger, D.: Alkaloids Derived from Tryptophan and Anthranilic Acid. In: Encyclopedia of Plant Physiology, New Series, Vol. 8 (Bell, E. A., B. V. Charlwood, ed.), p. 128. Berlin-Heidelberg: Springer-Verlag. 1980.

    Google Scholar 

  84. Gröger, D.: Anthranilic Acid as Precursor of Alkaloids. Lloydia 32, 221 (1969).

    Google Scholar 

  85. Gröger, D.: Chinazolinalkaloide. In: Biosynthese der Alkaloide (Mothes, K., H. R. Schütte, ed.), p. 551. Berlin: VEB Deutscher Verlag der Wissenschaften. 1969.

    Google Scholar 

  86. Johne, S., and D. Gröger: Alkaloide in Linaria-Arten. Pharmazie 23, 35 (1968).

    CAS  Google Scholar 

  87. Gröger, D., and S. Johne: Zur Analytik und Biochemie der Alkaloide von Adhatoda vasica Nees. In: Festschrift K. Mothes, p. 205. Jena: G. Fischer Verlag. 1965.

    Google Scholar 

  88. Gröger, D., and S. Johne: Zur Biosynthese einiger Alkaloide von Glycosmis arborea (Rutaceae). Z. Naturforsch. 23b, 1072 (1968).

    Google Scholar 

  89. Grundon, M. F.: Quinazoline Alkaloids. Alkaloids 6, 108 (1976); 8, 83 (1978); 9, 85 (1979); 10, 80 (1980); 12, 88 (1982) and in other chapters of this periodical.

    Google Scholar 

  90. Gunatilaka, A. A. L., S. Sotheeswaran, S. Balasubramaniam, A. I. Chandrasekara, and H. T. B. Sriyani: Studies on Medicinal Plants of Sri Lanka. Ill: Pharmacologically Important Alkaloids of Some Sida Species. Planta Med. 39, 66 (1980).

    CAS  Google Scholar 

  91. Gupta, O. P., K. K. Anand, B. J. R. Ghatak, and C. K. Atal: Vasicine, Alkaloid of Adhatoda vasica, a Promising Uterotonic Abortifacient. Indian J. Exp. Biol. 16, 1075 (1978).

    CAS  Google Scholar 

  92. Hagiwara, Y., M. Kurihara, and N. Yoda: Intramolecular Rearrangement — IV. Intramolecular Alkyl Rearrangements and Tautomerism of Quinazolinone Derivatives. Tetrahedron 25, 783 (1969).

    CAS  Google Scholar 

  93. Hart, N. K., S. R. Johns, and J. A. Lamberton: The Identification of a Minor Alkaloid of Mackinlaya macrosciadia (Araliaceae) as Deoxyvasicinone. Aust. J. Chem. 24, 223 (1971).

    CAS  Google Scholar 

  94. Hearn, J. M., R. A. Morton, and J. C. E. Simpson: Ultra-violet Absorption Spectra of Some Derivatives of Quinoline, Quinazoline, and Cinnoline. J. Chem. Soc. 1951, 3318.

    Google Scholar 

  95. Hikino, H., S. Nabetani, and T. Takemoto: Structure and Biosynthesis of Chrysogine, a Metabolite of Penicillium chrysogenum. Yakugaku Zasshi 93,619 (1973). (Japan) [Chem. Abstr. 79, 40 922 q (1973)].

    Google Scholar 

  96. Hill, R. K., and A. G. Edwards: The Absolute Configuration of Febrifugine. Chem. and Ind. 1962, 858.

    Google Scholar 

  97. Holubek, J., and O. Strouf (eds.): Spectral Data and Physical Constants of Alkaloids, Vol. I. Prag: Publishing House of the Czechoslovak Academy of Sciences. 1965.

    Google Scholar 

  98. Hooper, D.: Blätter von Adhatoda Vasica, Nees. Phar. J. 18, 841 (1888).

    Google Scholar 

  99. Horvath-Dora, K., and O. Clauder: Alkaloids Containing the Indolo[2,3-c]quinazolino[3,2-a]pyridine Skeleton. III. 3,14-Dihydrorutaecarpine. Acta Chim. Acad. Hung. 84, 93 (1975).

    CAS  Google Scholar 

  100. Huq, E. M., M. Ikram, and S. A. Warsi: Chemical Composition of Adhatoda vasica. II. Pakistan J. Sci. Ind. Res. 10, 224 (1967) [Chem. Abstr. 69, 16 807d (1968)].

    Google Scholar 

  101. Jain, M. P., and V. K. Sharma: Phytochemical Investigation of Roots of Adhatoda vasica. Planta Med. 46, 250 (1982).

    CAS  Google Scholar 

  102. Jang, C. S., F. Y. Fu, C. Y. Wang, K. C. Huang, G. Lu, and T. C. Chou: Ch’ang Shan, a Chinese Antimalarial Herb. Science 103, 59 (1946).

    CAS  Google Scholar 

  103. Jarrah, M. Y., and V. Thaller: 300 MHz 1H N.m.r. Spectra of Indolo[2,l-b]quinazoline-6,12-dione, Tryptanthrine, and its 2- and 8-Chloro-derivatives. J. Chem. Res. (S) 1980, 186; J. Chem. Res. (M) 1980, 2601.

    Google Scholar 

  104. Johne, S.: Search for Pharmaceutically Interesting Quinazoline Derivatives: Efforts and Results (1969–1980). Progr. Drug Res. 26, 259 (1982).

    CAS  Google Scholar 

  105. Johne, S., and D. Gröger: Natürlich vorkommende Chinazolin-Derivate. Pharmazie 25, 22 (1970).

    CAS  Google Scholar 

  106. Johne, S., D. Gröger, and M. Hesse: Neue Alkaloide aus Adhatoda vasica Nees. Helv. Chim. Acta 54, 826 (1971).

    CAS  Google Scholar 

  107. Johne, S., B. Jung, D. Gröger, and R. Radeglia: Synthese und 13C-NMR- Spektroskopie einiger Pyrrolo[2,l-b]chinazoline. J. Prakt. Chem. 319, 919 (1977).

    CAS  Google Scholar 

  108. Johne, S., K. Waiblinger, and D. Gröger: Untersuchungen zur Biosynthese des Chinazolinalkaloids Peganin in Adhatoda vasica Nees. Pharmazie 28, 403 (1973).

    CAS  Google Scholar 

  109. Johne, S., K. Waiblinger, and D. Gröger: Zur Biosynthese des Chinazolin-Alkaloids Arborin. Eur. J. Biochem. 15, 415 (1970).

    CAS  Google Scholar 

  110. Johns, S. R., and J. A. Lamberton: Alkaloids of Mackinlaya Species (Family Araliaceae). J. Chem. Soc. Chem. Commun. 1965, 267.

    Google Scholar 

  111. Kametani, T.: Evodiamine. Japan. Kokai 7777,098 [Chem. Abstr. 87, 201 858f (1977)].

    Google Scholar 

  112. Kametani, T.: Rutecarpine. Japan. Kokai 7877,100 [Chem. Abstr. 89, 163836d (1978)].

    Google Scholar 

  113. Kametani, T., T. Higa, K. Fukumoto, and M. Koizumi: One-Step Synthesis of Evodiamine and Rutecarpine. Heterocycles 4, 23 (1976).

    CAS  Google Scholar 

  114. Kametani, T., C. V. Loc, T. Higa, M. Ihara, and K. Fukumoto: Studies on the Syntheses of Heterocyclic Compounds. Part 724. Total Syntheses of the Quinazolinone Alkaloids Glycorine, Glomerine, Homoglomerine, Crysogine, and Euxylophoricines A and C. J. Chem. Soc. Perkin Trans. I 1977, 2347.

    Google Scholar 

  115. Kametani, T., C. V. Loc, T. Higa, M. Koizumi, M. Ihara, and K. Fukumoto: Iminoketene Cycloaddition. 2. Total Syntheses of Arborine, Glycosminine, and Rutecarpine by Condensation of Iminoketene with Amides. J. Amer. Chem. Soc. 99, 2306 (1977).

    CAS  Google Scholar 

  116. Kametani, T., C. V. Loc, T. Higa, M. Koizumi, M. Ihara, and K. Fukumoto: Simple Synthesis of Quinazolone Alkaloids, Arborine and Rutecarpine Through Iminoketene. Heterocycles 4, 1487 (1976).

    CAS  Google Scholar 

  117. Kametani, T., C. V. Loc, T. Higa, T. Ohsawa, M. Koizumi, M. Ihara, and K. Fukumoto: The Synthesis of Quinazolinone Alkaloids Through Potential Iminoketene Intermediate. Heterocycles 12, 208 (1979).

    Google Scholar 

  118. Kametani, T., C. V. Loc, M. Ihara, and K. Fukumoto: Modified Total Synthesis of Arborine, Glycosminine, and Glomerine by Condensation of Sulfinamide Anhydride with Thioamides. Heterocycles 9, 1585 (1978).

    CAS  Google Scholar 

  119. Kametani, T., T. Higa, C. V. Loc, M. Ihara, M. Koizumi, and K. Fukumoto: Iminoketene Cycloaddition. 1. A Facile Synthesis of Quinazolone System by Condensation of Iminoketene with Imines — A Total Synthesis of Evodiamine and Rutaecarpine by Retro Mass-Spectral Synthesis. J. Amer. Chem. Soc. 98, 6186 (1976).

    CAS  Google Scholar 

  120. Kametani, T., T. Ohsawa, M. Ihara, and K. Fukumoto: Studies on the Syntheses of Heterocyclic Compounds. DCCLV. Iminoketene Cycloaddition. (4). Alternative Syntheses of 5,6,7,8-Tetrahydro-2,3-dimethoxy-8-oxoisoquinolo[l,2-b]quinazoline and Rutecarpine. Chem. Pharm. Bull. 26, 1922 (1978).

    CAS  Google Scholar 

  121. Nakagawa, M., M. Taniguchi, M. Sodeoka, M. Ito, K. Yamaguchi, and T. Hino: Total Synthesis of (+)- and (—)-Tryptoquivaline G by Biomimetic Double Cyclization. J. Amer. Chem. Soc. 105, 3709 (1983).

    CAS  Google Scholar 

  122. Kamikado, T., S. Murakoshi, and S. Tamura: Structure Elucidation and Synthesis of Alkaloids Isolated from Fruits of Evodia rutaecarpa. Agric. Biol. Chem. 42, 1515 (1978).

    CAS  Google Scholar 

  123. Karimov, A., M. V. Telezhenetskaya, and S. Yu. Yunusov: The Synthetic Analogs of the Peganum Alkaloids. I. Synthesis of the Methoxy- and Oxysubstituted Deoxyvasicinones and Deoxypeganines. Khim. Prir. Soedin. 1982, 498 (Russ).

    Google Scholar 

  124. Khan, A. W., A. P. Bhaduri, C. M. Gupta, and M. M. Dhar: Actinomycetes Studies: Part I — Microbiological Synthesis of Quinazomycin, an Echinomycin Analogue Containing One Quinazol-4-one-3-acetyl Residue. Indian J. Biochem. 6, 220 (1969).

    CAS  Google Scholar 

  125. Khashimov, KH. N., M. V. Telezhenetskaya, YA. V. Rashkes, and S. Yu. Yunusov: Pegamine, a New Alkaloid from Peganum harmala. Khim. Prir. Soedin. 1970, 453 (Russ).

    Google Scholar 

  126. Khashimov, KH. N., M. V. Telezhenetskaya, N. N. Sharakhimov, and S. Yu. Yunusov: Dynamics of the Accumulation of Alkaloids in Peganum harmala. Khim. Prir. Soedin. 1971, 382 (Russ).

    Google Scholar 

  127. Khashimov, KH. N., M. V. Telezhenetskaya, and S. Yu. Yunusov: Peganidine, a New Base from Peganum harmala. Khim. Prir. Soedin. 1969, 599 (Russ).

    Google Scholar 

  128. Kim,Y. H., G. B. Brown, H. S. Mosher, and F. A. Fuhrman: Tetrodotoxin: Occurrence in Atelopid Frogs of Costa Rica. Science 189, 151 (1975) and references cited therein.

    Google Scholar 

  129. Kishi, Y., T. Fukuyama, M. Aratani, F. Nakatsubo, T. Goto, S. Inoue, H. Tanino, S. Sugiura, and H. Kakoi: Synthetic Studies on Tetrodotoxin and Related Compounds. IV. Stereospecific Total Syntheses of DL-Tetrodotoxin. J. Amer. Chem. Soc. 94, 9219 (1972) and earlier papers.

    CAS  Google Scholar 

  130. Köhler, H.: Die Prüfung von Galega-Arten auf ihren Gehalt an Giftstoffen mit Hilfe biologischer Methoden. I. Die Giftigkeit der Geißraute (Galega officinalis L.) für Warmblüter. Biol. Zentralbl. 88, 165 (1969).

    Google Scholar 

  131. Koepfli, J. B., J. F. Mead, and J. A. Brockman: Alkaloids of Dichroa febrifuga. I. Isolation and Degradative Studies. J. Amer. Chem. Soc. 71, 1048 (1949).

    CAS  Google Scholar 

  132. Koretskaya, N. I.: Alkaloids of Peganum harmala. I. Isolation of Two New Alkaloids. Zhur. Obshchei Khim. 27, 3361 (1957) (Russ).

    Google Scholar 

  133. Koretskaya, N. I., and L. M. Utkin: Alkaloids of Peganum harmala. II. Structure of Two New Alkaloids. Zhur. Obshchei. Khim. 28, 1087 (1958) (Russ).

    Google Scholar 

  134. Kuffner, F., G. Lenneis, and H. Bauer: Über die Konstitution eines Nebenalkaloids aus Adhatoda vasica Nees. Monatsh. Chem. 91, 1152 (1960).

    CAS  Google Scholar 

  135. Lahiri, P. K., and S. N. Pradhan: Pharmacological Investigation of Vasicinol — An Alkaloid from Adhatoda vasica Nees. Indian J. Exp. Biol. 2, 219 (1964) and references cited therein.

    Google Scholar 

  136. Leete, E.: Alkaloid Biogenesis. In: Biogenesis of Natural Compounds (P. Bernfeld, ed.), 2nd. edn., p. 953. Oxford etc.: Pergamon Press. 1967.

    Google Scholar 

  137. Leonhard, N. J., and M. J. Martell: Laboratory Realization of the Schöpf-Oechler Scheme of Vasicine Synthesis. Tetrahedron Lett. 1960, 44.

    Google Scholar 

  138. Liljegren, D. J.: Biosynthesis of Quinazoline Alkaloids of Peganum harmala. Phytochemistry 10, 2661 (1971).

    CAS  Google Scholar 

  139. Liljegren, D. J.: The Biosynthesis of Quinazoline Alkaloids of Peganum harmala L. Phytochemistry 7, 1299 (1968).

    CAS  Google Scholar 

  140. Lupu, K. G.: Dynamics of the Alkaloid Levels in Linaria vulgaris and L. genistifolia Grown in Moldavia. Rast. Resur. 9,206 (1973) (Russ) [Chem. Abstr. 79,15 906 e (1973)].

    Google Scholar 

  141. Machemer, H.: Die Autoxydation der Metallkomplexe des Indigos. Ber. dtsch. Chem. Ges. 63, 1341 (1930) and references cited therein.

    Google Scholar 

  142. Mann, S.: Chinazolinderivate bei Pseudomonaden. Arch. Mikrobiol. 56, 324 (1967).

    CAS  Google Scholar 

  143. Mann, S.: Besonderheiten im Tryptophanstoffwechsel von Pseudomonas aeruginosa. Arch. Hygiene Bakteriol. 151, 474 (1967).

    CAS  Google Scholar 

  144. Manske, R. H. F. (ed.): The Alkaloids. New York: Academic Press.

    Google Scholar 

  145. The Quinazolinocarbolines. In: (133); Vol. VIII, p. 55 (1965).

    Google Scholar 

  146. Marion, L.: In: (133); Vol. II, p. 369 (1952).

    Google Scholar 

  147. Mehta, D. R., J. S. Naravane, and R. M. Desai: Vasicinone. A Bronchodilator Principle from Adhatoda vasica Nees. (N. O. Acanthaceae). J. Org. Chem. 28, 445 (1963).

    CAS  Google Scholar 

  148. Meinwald, Y. C., J. Meinwald, and Th. Eisner: 1,2-Dialkyl-4(3H)-quinazolinones in the Defensive Secretion of a Millipede (Glomeris marginata). Science 154, 390 (1966).

    CAS  Google Scholar 

  149. Möhrle, H., and P. Gundlach: Eine neue Synthese für DL-Vasicin. Tetrahedron Lett. 1970, 3249.

    Google Scholar 

  150. Möhrle, H., Chr. Kamper, and R. Schmid: Eine neue Synthese von Rutaecarpin. Arch. Pharm. 313, 990 (1980).

    Google Scholar 

  151. Möhrle, H., and C.-M. Seidel: Eine neue Synthese für Arborin und strukturanaloge 4(1 H)-Chinazolinone, 1. u. 2. Mitt. Arch. Pharm. 309, 503; 572 (1976).

    Google Scholar 

  152. Morris, R. C., W. E. Hanford, and R. Adams: Structure of Vasicine. III. Position of the Hydroxyl Group. J. Amer. Chem. Soc. 57, 951 (1935).

    CAS  Google Scholar 

  153. Mosher, H. S., F. A. Fuhrman, H. D. Buchwald, and H. G. Fischer: Tarichatoxin — Tetrodotoxin: A Potent Neurotoxin. Science 144, 1100 (1964).

    CAS  Google Scholar 

  154. Mukherjee, A., and P. K. Dey: Changes in Amino Acid Metabolism in Rat Brain Following Glycosine Administration. Indian J. Exp. Biol. 8, 263 (1970).

    CAS  Google Scholar 

  155. Munoz, G. G., and R. Madronero: Neue Kondensationsreaktionen mit Imidchloriden. Synthese von Pyrido[2,l-b]chinazolinen. Chem. Ber. 95, 2182 (1962).

    CAS  Google Scholar 

  156. Nakasoto, T., S. Asada, and K. Marui: Dehydroevodiamine, Main Alkaloid from the Leaves of Evodia rutaecarpa. Yakugaku Zasshi 82, 619 (1962) [Chem. Abstr. 58, 3470 b (1963)].

    Google Scholar 

  157. Ohnuma, T., Y. Kimura, and Y. Ban: Synthetic Studies on Oxindole Spiro-Lactones with Thallium (III) Trinitrate: Formal Synthesis of (±)-Tryptoquivaline G. Tetrahedron Lett. 22, 4969 (1981).

    CAS  Google Scholar 

  158. Onaka, T.: A General Three-Step Synthesis of Pyrrolidino[2,l-b]quinazolone Alkaloids via Biogenetically Patterned Path. Tetrahedron Lett. 1971, 4387.

    Google Scholar 

  159. Openshaw, H. T.: The Quinazoline Alkaloids. In: (133); Vol. Ill, p. 101 (1953); Vol. VII, p. 247 (1960).

    Google Scholar 

  160. Oripov, E., L. M. Yun, Kh. M. Shakhidoyatov, and Ch. Sh. Kadyrov: Some Reactions of α-Hydroxy- and α-Dimethylaminoformylidene-2,3-polymethylene-3,4- dihydro-4-quinazolinones. Khim. Prir. Soedin. 1978, 603 (Russ).

    Google Scholar 

  161. Pachter, I. J., R. J. Mohrbacher, and D. E. Zacharias: The Chemistry of Hortiamine and 6-Methoxyrhetsinine. J. Amer. Chem. Soc. 83, 635 (1961).

    CAS  Google Scholar 

  162. Pachter, I. J., R. F. Raffauf, G. E. Ullyot, and O. Ribeiro: Die Trennung und Identifizierung der Alkaloide von Hortia arborea. Angew. Chem. 69, 687 (1957).

    Google Scholar 

  163. Pachter, I. J., R. F. Raffauf, G. E. Ullyot, and O. Ribeiro: The Alkaloids of Hortia arborea Engl. J. Amer. Chem. Soc. 82, 5187 (1960).

    Google Scholar 

  164. Pachter, I. J., and G. Suld: The Structure and Synthesis of Rhetsinine. J. Org. Chem. 25, 1680 (1960).

    CAS  Google Scholar 

  165. Pakrashi, S. C., and J. Bhattacharyya: Indian Medicinal Plants. IV. Further Alkaloids from Glycosmis arborea. J. Sci. Ind. Res. (India) 21B, (1), 49 (1962).

    Google Scholar 

  166. Pakrashi, S. C., and J. Bhattacharyya: Studies on Indian Medicinal Plants. XIV. Interrelationships among the Quinazoline Alkaloids from Glycosmis arborea (Roxb.) DC. Tetrahedron 24, 1 (1968).

    CAS  Google Scholar 

  167. Pakrashi, S. C., and J. Bhattacharyya: Recent Advances in the Chemistry of Rutaceae Alkaloids. J. Sci. Ind. Res. (India) 24, 293 (1963).

    Google Scholar 

  168. Pakrashi, S. C., and J. Bhattacharyya: Studies on Indian Medicinal Plants. Part V: Isolation of Minor Alkaloids from Glycosmis arborea (Roxb.) DC. Ann. Biochem. Exptl. Med. 23, 123 (1963).

    CAS  Google Scholar 

  169. Pakrashi, S. C., J. Bhattacharyya, L. F. Johnson, and H. Budzikiewicz: Studies of Indian Medicinal Plants — VI. Structures of Glycosmicine, Glycorine and Glycosminine, the Minor Alkaloids from Glycosmis arborea (Roxb.) DC. Tetrahedron 19, 1011 (1963).

    CAS  Google Scholar 

  170. Pakrashi, S. C., A. De, and S. Chattopadhyay: Studies on 4-Quinazolinones: Part I — Convenient Synthesis of Glycosminine and Arborine, the Alkaloids from Glycosmis arborea and Related 4-Quinazolinones. Indian J. Chem. 6, 472 (1968).

    CAS  Google Scholar 

  171. Palazzo, S., L. I. Giannola, and S. Caronna: Reaction of Formation of 2-Substituted 4-Quinazolinones in Polyphosphoric Acid: Synthesis of Glycosminine. Atti Accad. Sci. Lett. Arti Palermo, Parte 1, 34, 339 (1976) [Chem. Abstr. 89, 43309n (1978)].

    Google Scholar 

  172. Pallares, E. S.: The Structure of the Water-Insoluble Pigment of the Bark of “Sangre de Drago”. Arch. Biochem. 10, 235 (1946).

    CAS  Google Scholar 

  173. Petersen, S., and E. Tietze: Die Reaktion cyclischer Lactimäther mit Amino-carbonsäuren. Justus Liebigs Ann. Chem. 623, 166 (1959).

    CAS  Google Scholar 

  174. Plugar, V. N., T. T. Gorovits, N. Tulyaganov, and Ya. V. Rashkes: Transformations of 4-Quinazolinone Group Alkaloids in Animals. Khim. Prir. Soedin. 1977, 250 (Russ).

    Google Scholar 

  175. Plekhanova, N. V., and S. T. Aktanova: Alkaloids of Peganum harmala. Issled. Flory Kirgizii na Alkaloidonosnost, Akad. Nauk Kirg. SSR, Inst. Organ. Khim. 1965, 57 (Russ) [Chem. Abstr. 64, 11550 f (1966)].

    Google Scholar 

  176. Plekhanova, N. V., and G. P. Sheveleva: Alkaloids of Linaria transiliensis and Linaria vulgariformis. Issled. Flory Kirgizii na Alkaloidonosnost, Akad. Nauk Kirg. SSR, Inst. Organ. Khim. 1965, 54 (Russ) [Chem. Abstr. 64, 11550e (1966)].

    Google Scholar 

  177. Plugar, V. N., Ya. V. Rashkes, and Kh. M. Schakhidoyatov: Mass Spectra of 2,3- Polymethylene-3,4-dihydro-4-quinazolones with Substituents at C9. Khim. Prir. Soedin. 1979, 180 (Russ).

    Google Scholar 

  178. Plugar, V. N., Ya. V. Rashkes, and Kh. M. Schakhidoyatov: Comparison of the Mass Spectra of 2,3-Polymethylene-l,2,3,4-tetrahydro-quinazol-4-ones. Khim. Prir. Soedin. 1978, 414 (Russ).

    Google Scholar 

  179. Plugar, V. N., Ya. V. Rashkes, and N. Tulyaganov: Quantitative Analysis of the Components of Desoxypeganine and Desoxyvasicinone Metabolites. Khim. Prir. Soedin. 1981, 201 (Russ).

    Google Scholar 

  180. Prakash, A., R. K. Varma, and S. Ghosal: Alkaloidal Constituents of Sida acuta, S. humilis, S. rhombifolia, and S. spinosa. Planta Med. 43, 384 (1981).

    CAS  Google Scholar 

  181. Price, J. R.: Quinazoline Alkaloids. Fortschr. Chem. org. Naturstoffe 13, 330 (1956).

    Google Scholar 

  182. Rajagopalan, T. R., S. Bhattacharji, and M. L. Dhar: Proceedings, Symposium on Drugs and Antibiotics ( Defence Research Laboratory, Kanpur ), 1961, 121.

    Google Scholar 

  183. Rashkes, Ya. V., M. V. Telezhenetskaya, V. N. Plugar, and S. Yu. Yunusov: Mass Spectra of Tetrahydroquinazoline and Tetrahydroquinazolin-4-one Derivatives. Khim. Prir. Soedin. 1977, 378 (Russ).

    Google Scholar 

  184. Rhee, R. P., and J. D. White: Synthesis of Cyclopenin and Glycosminine from Phenylpyruvic Acid. J. Org. Chem. 42, 3650 (1977).

    CAS  Google Scholar 

  185. Robinson, R.: The Structural Relations of Natural Products. Oxford: Clarendon Press. 1955.

    Google Scholar 

  186. Rosenfeld, A. D., and D. G. Kolesnikov: Über 1-Peganin aus Blüten und Stengeln von Peganum harmala L., Bemerkungen zu den Arbeiten von E. Späth über Peganin. Ber. dtsch. Chem. Ges. 69, 2022 (1936) and references cited therein.

    Google Scholar 

  187. Sakamoto, S., and K. Samejima: Preparation of Specific Antibody to 2,3-Trimethylene- 4-quinazolone for the Immunoassay of Δ1-Pyrroline. Chem. Pharm. Bull. 28, 916 (1980).

    CAS  Google Scholar 

  188. Sakamoto, S., and K. Samejima: Determination of Δ1-Pyrroline as 2,3-Trimethylene-4-quinazolone. Chem. Pharm. Bull. 27, 2220 (1979).

    CAS  Google Scholar 

  189. Sarkar, M., and D. P. Chakraborty: Some Minor Constituents from Glycosmis pentaphylla. Phytochemistry 16, 2007 (1977).

    Google Scholar 

  190. Glycophymoline, a New Minor Quinazoline Alkaloid from Glycosmis pen¬taphylla. Phytochemistry 18, 694 (1979).

    Google Scholar 

  191. Schäfer, J., and M. Stein: Untersuchungen über toxische Inhaltsstoffe bei Galega officinalis L. Biol. Zentralbl. 88, 755 (1969).

    Google Scholar 

  192. Schäfer, J., and M. Stein: Über die Variabilität von Inhaltsstoffen in der Geißraute (Galega officinalis L.). Naturwissenschaften 54, 205 (1967).

    Google Scholar 

  193. Schildknecht, H., and W. F. Wenneis: Über Arthropoden-Abwehrstoffe XXV. Anthranilsäure als Precursor der Arthropoden-Alkaloide Glomerin and Homoglomerin. Tetrahedron Lett. 1967, 1815.

    Google Scholar 

  194. Schildknecht, H., and W. F. Wenneis: Über Arthropoden-(Insekten-)Abwehrstoffe XX. Strukturaufklärung des Glomerins. Z. Naturforsch. 21b, 552 (1966).

    CAS  Google Scholar 

  195. Schildknecht, H., W. F. Wenneis, K. H. Weis, and U. Maschwitz: Glomerin, ein neues Arthropoden-Alkaloid. Z. Naturforsch. 21b, 121 (1966).

    CAS  Google Scholar 

  196. Schindler, F., and H. Zähner: Tryptanthrin, ein von Tryptophan abzuleitendes Antibioticum aus Candida lipolytica. Arch. Mikrobiol. 79, 187 (1971).

    CAS  Google Scholar 

  197. Schöpf, C., A. Komzak, F. Braun, and E. Jacobi: Über die Polymeren des Δ1-Piperideins. Justus Liebigs Ann. Chem. 559, 1 (1948).

    Google Scholar 

  198. Schreiber, K., O. Aurich, and K. Pufahl: Isolierung von (+)-Peganin aus der Geißraute, Galega officinalis L. Arch. Pharm. 295, 271 (1962).

    CAS  Google Scholar 

  199. Sen, A. K., S. B. Mahato, and N. L. Dutta: Couroupitine A, a New Alkaloid from Couroupita guianensis. Tetrahedron Lett. 1974, 609.

    Google Scholar 

  200. Shakhidoyatov, Kh., A. Irishbaeva, and Ch. Sh. Kadyrov: Synthesis of Desoxypeganine and its Derivatives. Khim. Prir. Soedin. 1974, 681 (Russ).

    Google Scholar 

  201. Shakhidoyatov, Kh., A. Irishbaeva, E. Oripov, and Ch. Sh. Kadyrov: Quinazolines. VII. Synthesis of 6-Nitro-, Amino-, and 9,9-Dibromodesoxyvasicinone. Khim. Prir. Soedin. 1976, 557 (Russ).

    Google Scholar 

  202. Shakhidoyatov, Kh. M., and Ch. Sh. Kadyrov: Quinazolines. XII. 4-Thio Analogs of Desoxyvasicinone, its Derivatives and Homologs. Khim. Prir. Soedin. 1977, 668 (Russ).

    Google Scholar 

  203. Shakhidoyatov, Kh. M., and Ch. Sh. Kadyrov: Quinazolines. X. Synthesis of Methyl-enebis(6,6′-desoxyvasicinone) and its Homologs. Khim. Prir. Soedin. 1977, 544 (Russ).

    Google Scholar 

  204. Shakhidoyatov, Kh. M, Ya. Yamankulov, and Ch. Sh. Kadyrov: Quinazolines. XI. Condensation of Desoxyvasicinone with Aldehydes. Khim. Prir. Soedin. 1977, 552 (Russ).

    Google Scholar 

  205. Sharma, R. L., R. K. Gupta, B. K. Chowdhury, K. L. Dhar, and C. K. Atal: Syntheses of Some Vasicine Analogues. Indian J. Chem. 18B, 449 (1979).

    Google Scholar 

  206. Sharma, V. K., and M. P. Jain: Synthesis of Vasicinone Derivatives. Indian J. Chem. 21B, 75 (1982).

    Google Scholar 

  207. Sheumack, D. D., M. E. H. Howden, I. Spence, and R. J. Quinn: Maculotoxin: A Neurotoxin from the Venom Glands of the Octopus Hapalochlaena maculosa Identified as Tetrodotoxin. Science 199, 188 (1978).

    CAS  Google Scholar 

  208. Siddiqui, S.: A Reinvestigation of the Alkaloidal Constituents of Peganum harmala. Pakistan J. Sci. Ind. Res. 5, 207 (1962) [Chem. Abstr. 59, 5213 (1963)].

    CAS  Google Scholar 

  209. Snieckus, V. A.: Quinazoline Alkaloids. Alkaloids 2, 91 (1972); 3, 112 (1973); 4, 124 (1974); 5, 108 (1975).

    Google Scholar 

  210. Southwick, P. L., and L. Casanova: A New Synthesis of dl-Vasicine and a Methoxy Analog. J. Amer. Chem. Soc. 80, 1168 (1958).

    CAS  Google Scholar 

  211. Späth, E.: Über das Peganin (Vasicin). Monatsh. Chem. 72, 115 (1939).

    Google Scholar 

  212. Späth, E., and F. Kesztler-Gandini: Über ein Nebenalkaloid aus Adhatoda vasica Nees. Monatsh. Chem. 91, 1150 (1960).

    Google Scholar 

  213. Späth, E., F. Kuffner, and N. Platzer: Synthese und Konstitution des Peganins (Vasicins). Ber. dtsch. Chem. Ges. 68, 699 (1935).

    Google Scholar 

  214. Späth, E., and N. Platzer: Eine neue Synthese von Pegen-(9) und Peganin (IX. Mitteil, über Peganin). Ber. dtsch. Chem. Ges. 69, 255 (1936).

    Google Scholar 

  215. Späth, E., and N. Platzer: Über Derivate des Peganins und ihre Ring-Homologen (VIII. Mitteil, über Peganin). Ber. dtsch. Chem. Ges. 68, 2221 (1935).

    Google Scholar 

  216. Stephen, T., and H. Stephen: The Beckmann Rearrangement of cyclo Pentanone Oxime. J. Chem. Soc. 1956, 4694.

    Google Scholar 

  217. Strong, P. N., and J. F. W. Keana: Modification of Tetrodotoxin With Succinic Anhydride. Bioorg. Chem. 5, 255 (1976).

    CAS  Google Scholar 

  218. Szulzewsky, K., E. Höhne, S. Johne, and D. Gröger: Bestimmung der Molekül- und Kristallstruktur sowie der Absolutkonfiguration von Peganin. J. Prakt. Chem. 318, 463 (1976).

    CAS  Google Scholar 

  219. Takeda Chemical Industries, Ltd.: Tryptanthrin. Jpn. Kokai Tokkyo Koho 80 47,684 (1980) [Chem. Abstr. 93, 186400 d (1980)].

    Google Scholar 

  220. Telezhenetskaya, M. V., Kh. N. Kashimov, and S. Yu. Yunusov: Peganol, a New Alkaloid from Peganum harmala. Khim. Prir. Soedin. 1971, 849 (Russ).

    Google Scholar 

  221. Telezhenetskaya, M. V., and S. Yu. Yunusov: Alkaloids of Peganum harmala. Khim. Prir. Soedin. 1977, 731 (Russ).

    Google Scholar 

  222. 208a.Toth, G., K. Horváth-Dora, O. Clauder, and H. Duddeck: Alkaloide mit Indolo[2′,3′:3,4]pyrido[2,1-b]chinazolin-Struktur. VII. Synthese und Untersuchungen des cis- und trans-Hexahydrorutaecarpins. Justus Liebigs Ann. Chem. 1977, 529.

    Google Scholar 

  223. Tscheche, T., and W. Werner: Evocarpin, ein neues Alkaloid aus Evodia rutaecarpa. Tetrahedron 23, 1873 (1967).

    Google Scholar 

  224. Tsien, R. Y., D. P. L. Green, S. R. Levinson, B. Rudy, and J. K. M. Sanders: A Pharmacologically Active Derivative of Tetrodotoxin. Proc. R. Soc. London, Ser. B 191, 555 (1975).

    CAS  Google Scholar 

  225. Springer, J. P.: The Absolute Configuration of Nortryptoquivaline. Tetrahedron Lett. 1979, 339.

    Google Scholar 

  226. Tsuda, K.: Über Tetrodotoxin, Giftstoff der Bowlfische. Naturwissenschaften 53, 171 (1966).

    CAS  Google Scholar 

  227. Tsuda, K., S. Ikuma, M. Kawamura, R. Tachikawa, K. Sakai, C. Tamura, and O. Amakasu: The Structures of Tetrodotoxin and its Derivatives. Chem. Pharm. Bull. 12, 1357 (1964) and references cited therein.

    CAS  Google Scholar 

  228. Vasudevan, T. N., and M. Luckner: Alkaloide aus Ruta angustifolia Pers., Ruta chalepensis L., Ruta graveolens L. und Ruta montana Mill. Pharmazie 23, 520 (1968).

    CAS  Google Scholar 

  229. Vincent, M., J. Maillard, and M. Benard: Structure and Properties of Alkyl Iodides of Alkyldihydro-4-quinazolones. Bull. Soc. Chim. Fr. 1963, 119.

    Google Scholar 

  230. Waiblinger, K., S. Johne, and D. Gröger: Zur Biosynthese des Pyrrolidinringes in Peganin. Phytochemistry 11, 2263 (1972).

    CAS  Google Scholar 

  231. Waletzky, E., G. Berkelhammer, and S. Kantor: Quinazolinones for Treating Coccidiosis. US Pat. 3,320,124 (1967) [Chem. Abstr. 68, 39 647v (1968)].

    Google Scholar 

  232. Waterman, P. G.: Alkaloids of the Rutaceae. Distribution and Systematic Significance. Biochem. Syst. Ecol. 3, 149 (1975).

    CAS  Google Scholar 

  233. Williamson, T. A.: In: Heterocyclic Compounds (R. C. Elderfield, ed.), Vol. VI, p. 351. New York: Wiley. 1957. — Landquist, J. K.: In: Chemistry of Carbon Compounds (E. H. Rodd, ed.), Vol. IVB, p. 1308. London: Elsevier. 1959.

    Google Scholar 

  234. Woodward, R. B.: Structure of Tetrodotoxin. Pure Appl. Chem. 9, 49 (1964).

    CAS  Google Scholar 

  235. Woodward, R. B., and J. Z. Gougoutas: The Structure of Tetrodotoxin. J. Amer. Chem. Soc. 86, 5030 (1964).

    CAS  Google Scholar 

  236. Yamazaki, M., H. Fujimoto, and E. Okuyama: Structure Determination of Six Metabolites, Tryptoquivaline E, F, G, H, I and J from Aspergillus fumigatus. Chem. Pharm. Bull. 26, 111 (1978).

    CAS  Google Scholar 

  237. Yamazaki, M., H. Fujimoto, and E. Okuyama: Structure of Tryptoquivaline C (FTC) and D (FTD). Novel Fungal Metabolites from Aspergillus fumigatus. Chem. Pharm. Bull. 25, 2554 (1977).

    CAS  Google Scholar 

  238. Yamazaki, M., H. Fujimoto, and E. Okuyama: Structure Determination of Six Tryptoquivaline Related Metabolites from Aspergillus fumigatus. Tetrahedron Lett. 1976, 2861.

    Google Scholar 

  239. Yamazaki, M., and A. Ikuta: Biosynthesis of Evodia Alkaloids. Tetrahedron Lett. 1966, 3221.

    Google Scholar 

  240. Yamazaki, M., A. Ikuta, T. Mori, and T. Kawana: Biosynthesis of Evodia Alkaloids. II. The Participation of C1-Unit to the Formation of Indoloquinazoline Alkaloids. Tetrahedron Lett. 1967, 3317.

    Google Scholar 

  241. Yamazaki, M., and T. Kawana: Isolation of Hydroxyevodiamine (Rhetsinine) from the Fruits of Evodia rutaecarpa Hook fil. et Thomson. Yakugaku Zasshi 87, 608 (1967) (Japan) [Chem. Abstr. 67, 64 601 n (1967)].

    Google Scholar 

  242. Yamazaki, M., E. Okuyama, and Y. Maebayashi: Isolation of Some New Tryptoquivaline — related Metabolites from Aspergillus fumigatus. Chem. Pharm. Bull. 27, 1611 (1979).

    CAS  Google Scholar 

  243. Yvore, P., N. Foure, J. Aycardi, and G. Bennejean: Efficiency of Stenorol in the Chemoprophylaxis of Avian Coccidiosis. Reel. Med. Vet. 150, 495 (1974).

    CAS  Google Scholar 

  244. Zabolotnaya, E. S., and L. N. Safronich: Alkaloids of Dichroa febrifuga Introduced into the USSR. Lekarstv. Rasteniya 1969 (15), 356 [Chem. Abstr. 76, 32240p (1972)].

    Google Scholar 

  245. Zharekeev, B. Kh., Kh. N. Khashimov, M. V. Telezhenetskaya, and S. Yu. Yunusov: New Alkaloids from Peganum harmala. Khim. Prir. Soedin. 1974, 264 (Russ).

    Google Scholar 

  246. Zharekeev, B. Kh., M. V. Telezhenetskaya, and S. Yu. Yunusov: Deoxypeganidine, a New Alkaloid from Peganum harmala. Khim. Prir. Soedin. 1973, 279 (Russ).

    Google Scholar 

  247. Ziegler, E., W. Steiger, and Th. Kappe: Synthesen von Heterocyclen, 130. Mitt.: Über das Glomerin und das Arborin. Monatsh. Chem. 100, 948 (1969).

    CAS  Google Scholar 

  248. Zutschi, U., P. G. Rao, A. Soni, O. P. Gupta, and C. K. Atal: Absorption and Distribution of Vasicine, a Novel Uterotonic. Planta Med. 40, 373 (1980).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Plant Biochemistry, The Academy of Sciences of the German Democratic Republic, Halle (Saale), German Democratic Republic

    S. Johne

Authors
  1. S. Johne
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Chemistry, The Florida State University, Tallahassee, Florida, USA

    W. Herz (Professor of Chemistry) (Professor of Chemistry)

  2. Biologisches Institut II, Lehrstuhl für Biochemie der Pflanzen, Albert-Ludwigs-Universität, Freiburg i. Br., Federal Republic of Germany

    H. Grisebach

  3. Chemistry Department, The University, Glasgow, Scotland

    G. W. Kirby Sc. D. (Regius Professor of Chemistry) (Regius Professor of Chemistry)

  4. Institut für Organische Chemie, Universität Basel, Basel, Switzerland

    Ch. Tamm

Rights and permissions

Reprints and permissions

Copyright information

© 1984 Springer-Verlag/Wien

About this chapter

Cite this chapter

Johne, S. (1984). The Quinazoline Alkaloids. In: Herz, W., Grisebach, H., Kirby, G.W., Tamm, C. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 46. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8759-3_4

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-8759-3_4

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-8761-6

  • Online ISBN: 978-3-7091-8759-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation