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Die Chemie der Tetracycline

  • H. Von Muxfeldt
  • R. Bangert
Chapter
  • 35 Downloads
Part of the Fortschritte Der Chemie Organischer Naturstoffe book series (FORTCHEMIE (closed), volume 21)

Zusammenfassung

Tetracycline sind blaβgelb gefärbte, kristallisierte Antibiotika, die von verschiedenen Streptomyces-Stämmen produziert werden und sich nicht nur durch besonders vorteilhafte chemotherapeutische Eigenschaften auszeichnen (14, 48, 35, 73), sondern zugleich eine neue Klasse strukturell interessanter Naturstoffe darstellen, deren chemisches und physikalisches Verhalten Gegenstand eingehender Untersuchungen verschiedener Laboratorien während des letzten Jahrzehnts gewesen ist.

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Literaturverzeichnis

  1. 1.
    André, T. and S. Ullberg: Radioactive Tetracycline. J. Amer. Chem. Soc.79, 494 (1957).CrossRefGoogle Scholar
  2. 2.
    Beereboom, J. J., J. J. Ursprung, H. H. Rennhard and C. R. Stephens: Further 6-Deoxytetracycline Studies: Effect of Aromatic Substituents on Biological Activity. J. Amer. Chem. Soc.82, 1003 (1960).CrossRefGoogle Scholar
  3. 3.
    Blackwood, R. K., J. J. Beereboom, H. H. Rennhard, M. Schach von Wittenau and C. R. Stephens: 6;-Methylenetetracyclines. I. A New Class of Tetracycline Antibiotics. J. Amer. Chem. Soc.83, 2773 (1CrossRefGoogle Scholar
  4. 4.
    Blackwood, R. K., H. H. Rennhard and C. R. Stephens: Some Transformations at the 12 a-Position in the Tetracycline Series. J. Amer. Chem. Soc.82, 5194 (1960).CrossRefGoogle Scholar
  5. 5.
    Boothe, J. H., G. E. Bonvicino, C. W. Waller, J. P. Petisi, R. W. Wilkinson and R. W. Broschard: Chemistry of the Tetracycline Antibiotics. I. Quaternary Derivatives. J. Amer. Chem. Soc.80, 1654 (1958).CrossRefGoogle Scholar
  6. 6.
    Boothe, J. H., A. Green, J. P. Petisi, R. G. Wilkinson and C. W. Waller: Demethyltetracyclines. Synthesis of a Degradation Product. J. Amer. Chem. Soc.79, 4564 (1957).CrossRefGoogle Scholar
  7. 7.
    Boothe, J. H., J. J. Hlavka, J. P. Petisi and J. L. Spencer: 6-Deoxytetra-cyclines. I. Chemical Modification by Electrophilic Substitution. J. Amer. Chem. Soc.82, 1253 (1960).CrossRefGoogle Scholar
  8. 8.
    Boothe, J. H., A. S. Kende, T. L. Fields and R. G. Wilkinson: Total Synthesis of Tetracyclines. I. (±)-Dedimethylamino-12a-deoxy-6-demethyl-anhydrochlorotetracycline. J. Amer. Chem. Soc.81, 1006 (1959).CrossRefGoogle Scholar
  9. 8a.
    Brockmann, H.: Die Actinomycine. Fortschr. Chem. organ. Naturst.18, 1 (1960).Google Scholar
  10. 9.
    Broschard, R. W., A. C. Dornbush, S. Gordon, B. L. Hutchings, A. R. Kohler, G. Krupka, S. Kushner, D. V. Lefimine and C. Pidacks: Aureo-mycin, a New Antibiotic. Science (Washington) 109, 199 (1949).CrossRefGoogle Scholar
  11. 10.
    Conover, L. H.: Progress in the Chemistry of Oxytetracycline and Related Compounds. Chem. Soc.(London), Spec. Publ. No. 5, p. 73 (1956).Google Scholar
  12. 11.
    Conover, L. H., K. Butler, J. D. Johnston, J. J. Korst and R. B. Woodward: The Total Synthesis of 6-Demethyl-6-deoxy-tetracycline. J. Amer. Chem. Soc.84, 3222 (1962).CrossRefGoogle Scholar
  13. 12.
    Doerschuk, A. P., B. A. Bitler and J. R. D. Mccormick: Reversible Isomerizations in the Tetracycline Family. J. Amer. Chem. Soc.77, 4687 (1955).CrossRefGoogle Scholar
  14. 13.
    Doerschuk, A. P., J. R. D. Mccormick, J. J. Goodman, S. A. Szumski, J. A. Growich, P. A. Miller, B. A. Bitler, E. R. Jensen, M. Matrishin, M. A. Petty and A. S. Phelps: Biosynthesis of Tetracyclines. I. The Halide Metabolism of Streptomyces aureofaciens Mutants. The Preparation and Characterization of Tetracycline, 7-Chloro36-tetracycline and 7-Bromotetra-cycline. J. Amer. Chem. Soc.81, 3069 (1959).CrossRefGoogle Scholar
  15. 14.
    Dowling, H. F.: Tetracycline. New York: Medical Encyclopedia, Inc. 1955.Google Scholar
  16. 15.
    Duggar, B. M.: Aureomycin—a New Antibiotic. Ann. New York Acad. Sci.51, 175 (1948).CrossRefGoogle Scholar
  17. 16.
    Fields, T. L., A. S. Kende and J. H. Boothe: Total Synthesis of Tetracyclines. II. Stereospecific Synthesis of (±)-Dedimethylamino-6-demethyl-6, 12 a-dideoxy-7-chlorotetracycline. J. Amer. Chem. Soc.82, 1250 (1960).CrossRefGoogle Scholar
  18. 17.
    Fields, T. L., A. S. Kende and J. H. Boothe:Total Synthesis of Tetracyclines. V. The Stereospecific Elaboration of the Tetracycline Ring System. J. Amer. Chem. Soc.83, 4612 (1961).CrossRefGoogle Scholar
  19. 18.
    Finlay, A. C, G. L. Hobby, S. Y. Plan, P. P. Regna, J. B. Routien, D. B. Seeley, G. M. Shull, B. A. Sobin, I. A. Solomons, J. W. Vinson and J. H. Kane: Terramycin, a New Antibiotic. Science (Washington) III, 85 (1950).CrossRefGoogle Scholar
  20. 18a.
    Gatenbeck, S.: The Biosynthesis of Oxytetracycline. Biochem. and Biophys. Res. Comm. 6, 422 (1961-62).CrossRefGoogle Scholar
  21. 19.
    Gottstein, W. J., W. F. Minor and L. C. Cheney: Carboxamido Derivatives of the Tetracyclines. J. Amer. Chem. Soc.81, 1198 (1959).CrossRefGoogle Scholar
  22. 20.
    Green, A. and J. H. Boothe: Chemistry of the Tetracycline Antibiotics. III. 1 2 a-Deoxy-tetracycline. J. Amer. Chem. Soc.82, 3950 (1960).CrossRefGoogle Scholar
  23. 21.
    Green, A., R. G. Wilkinson and J. H. Boothe: Chemistry of the Tetracycline Antibiotics. II. Bromination of Dedimethylamino-tetracyclines. J. Amer. Chem. Soc.82, 3946 (1960).CrossRefGoogle Scholar
  24. 22.
    Hirokawa, S., Y. O. Okaya, F. M. Lovell and R. Pepinsky: Abstracts Amer. Cryst. Assoc.Meeting, Cornell Univ., Juli 1959, p. 44.Google Scholar
  25. 23.
    Hlavka, J. J. and D. A. Buyske: Radioactive y-Iodo-6-deoxy-tetracycline in Tumor Tissue. Nature (London) 186, 1064 (1960).Google Scholar
  26. 24.
    Hlavka, J. J., H. Krazinski and J. H. Boothe: The 6-Deoxytetracyclines. IV. A Photochemical Displacement of a Diazonium Group. J. Organ. Chem. (USA) 27, 3674 (1962).CrossRefGoogle Scholar
  27. 25.
    Hlavka, J. J., A. Schneller, H. Krazinski and J. H. Boothe: The 6-Deoxytetracyclines. III. Electrophilic and Nucleophilic Substitution. J. Amer. Chem. Soc.84, 1426 (1962).CrossRefGoogle Scholar
  28. 26.
    Hochstein, F. A., M. Schach VON Wittenau, F. W. Tanner, Jr. and K. Murai: 2-Acetyl-2-decarboxamido-oxytetracycline. J. Amer. Chem. Soc.82, 5934 (1960).CrossRefGoogle Scholar
  29. 27.
    Hochstein, F. A., C. R. Stephens, L. H. Conover, P. P. Régna, R. Paster-nack, P. N. Gordon, F. J. Pilgrim, K. J. Brunings and R. B. Woodward: The Structure of Terramycin. J. Amer. Chem. Soc.75, 5455 (1953).CrossRefGoogle Scholar
  30. 28.
    Holmlund, C. E., W. W. Andres and A. J. Shay: Chemical Hydroxylation of 12 a-Deoxy-tetracycline. J. Amer. Chem. Soc.81, 4748 (1959).CrossRefGoogle Scholar
  31. 29.
    Holmlund, C. E., W. W. Andres and A. J. Shay:Microbiological Hydroxylation of 12 a-Deoxy-tetracycline. J. Amer. Chem. Soc.81, 4750 (1959).CrossRefGoogle Scholar
  32. 30.
    Hutchings, B. L., C. W. Waller, R. W. Broschard, C. F. Wolf, P. W. Fryth and J. H. Williams: Degradation of Aureomycin. V. Aureomycinic Acid. J. Amer. Chem. Soc.74, 4980 (1952).CrossRefGoogle Scholar
  33. 31.
    Hutchings, B. L., C. W. Waller, S. Gordon, R. W. Broschard, C. F. Wolf, A. A. Goldman and J. H. Williams: Degradation of Aureomycin. J. Amer. Chem. Soc.74, 3710 (1952).CrossRefGoogle Scholar
  34. 32.
    Kende, A. S., T. L. Fields, J. H. Boothe and S. Kushner: Total Synthesis of Tetracyclines. IV. Synthesis of an Anhydrotetracycline Derivative. J. Amer. Chem. Soc.83, 439 (1961).CrossRefGoogle Scholar
  35. 33.
    Kuhn, R. und K. Dury: 6-Acetyl-salicylsäure. Chem. Ber.84, 848 (1951).CrossRefGoogle Scholar
  36. 34.
    Kushner, S., J. H. Boothe, J. Morton II, J. Petisi and J. H. Williams: Synthesis of Degradation Products of Aureomycin. J. Amer. Chem. Soc.74, 3710 (1952).CrossRefGoogle Scholar
  37. 35.
    Lepper, M. H.: Terramycin. New York: Medical Encyclopedia, Inc. 1956.Google Scholar
  38. 36.
    Mccormick, J. R. D., S. M. Fox, L. L. Smith, B. A. Bitler, J. Reichenthal, V. E. Origoni, W. H. Müller, R. Winterbottom and A. P. Doerschuk: On the Nature of the Reversible Isomerizations Occurring in the Tetracycline Family. J. Amer. Chem. Soc.78, 3547 (1956).CrossRefGoogle Scholar
  39. 37.
    Mccormick, J. R. D., S. M. Fox, L. L. Smith, B. A. Bitler, J. Reichenthal, V. E. Origoni, W. H. Müller, R. Winterbottom and A. P. Doerschuk:Studies of the Reversible Epimerization Occurring in the Tetracycline Family. The Preparation, Properties and Proof of Structure of Some 4-epi-Tetracyclines. J. Amer. Chem. Soc.79, 2849 (1957).CrossRefGoogle Scholar
  40. 38.
    Mccormick, J. R. D., U. Hirsch, N. O. Sjolander and A. P. Doerschuk: Cosynthesis of Tetracyclines by Pairs of Streptomyces aureofaciens Mutants. J. Amer. Chem. Soc.82, 5006 (1960).CrossRefGoogle Scholar
  41. 59.
    Mccormick, J. R. D. und E. R. Jensen: Deutsches Bundespat. 1082905 [Chem. Abstr. 56, 4703 (1962)].Google Scholar
  42. 40.
    Mccormick, J. R. D., E. R. Jensen, P. A. Miller and A. P. Doerschuk: The 6-Deoxytetracyclines. Further Studies on the Relationship between Structure and Antibacterial Activity in the Tetracycline Series. J. Amer. Chem. Soc.82, 3381 (1960).CrossRefGoogle Scholar
  43. 41.
    McCormick, J. R. D., P. A. Miller, J. A. Growich, N. O. Sjolander and A. P. Doerschuk: TWO New Tetracycline-related Compounds: 7-Chloro-5 a(II a)-Dehydrotetracycline and 5 a-epi-Tetracycline. A New Route to Tetra-cycline. J. Amer. Chem. Soc.80, 5572 (1958).CrossRefGoogle Scholar
  44. 42.
    Mccormick, J. R. D., P. A. Miller, S. Johnson, N. Arnold and N. O. Sjolander: Biosynthesis of the Tetracyclines. IV. Biological Rehydration of the 5 a,6-Anhydrotetracyclines. J. Amer. Chem. Soc.84, 3023 (1962).CrossRefGoogle Scholar
  45. 43.
    Mccormick, J. R. D., J. Reichenthal, U. Hirsch and N. O. Sjolander: Biosynthesis of the Tetracyclines. III. A New Amino Acid from Streptomyces aureofaciens: (+)-trans-2,3-Dihydro-3-hydroxyanthranilic Acid. J. Amer. Chem. Soc.84, 3711 (1962).CrossRefGoogle Scholar
  46. 44.
    Mccormick, J. R. D., N. O. Sjolander, U. Hirsch, E. R. Jensen and A. P. Doerschuk: A New Family of Antibiotics: The Demethyl-tetracyclines. J. Amer. Chem. Soc.79, 4561 (1957).CrossRefGoogle Scholar
  47. 43.
    Mccormick, J. R. D., N. O. Sjolander, U. Hirsch, P. A. Miller, N. H. Arnold and A. P. Doerschuk: The Biological Reduction of 7-Chloro-5 a(IIa)-dehydrotetracycline to 7-Chloro-tetracycline by Streptomyces aureofaciens. J. Amer. Chem. Soc.80, 6460 (1958).CrossRefGoogle Scholar
  48. 46.
    Miller, M. W. and F. A. Hochstein: Isolation and Characterization of Two New Tetracycline Antibiotics. J. Organ. Chem.(USA) 27, 2525 (1962).CrossRefGoogle Scholar
  49. 47.
    Miller, P. A., N. O. Sjolander, S. Nalesnyk, N. Arnold, S. Johnson, A. P. Doerschuk and J. R. D. Mccormick: Cosynthetic Factor I, a Factor Involved in Hydrogen Transfer in Streptomyces aureofaciens. J. Amer. Chem. Soc.82, 5002 (1960).CrossRefGoogle Scholar
  50. 48.
    Musselman, M. M.: Aureomycin. New York: Medical Encyclopedia, Inc. 1956.Google Scholar
  51. 49.
    Muxfeldt, H.: Synthesen in der Tetracyclinreihe. Angew. Chem.74, 443 (1962). Syntheses in the Tetracycline Series. Angew. Chem. Internat. Ed. 1, 372 (1962).CrossRefGoogle Scholar
  52. 50.
    Muxfeldt, H.:Synthese tetracyclischer Abbauprodukte von Anhydrotetracyclinen. Chem. Ber.92, 3122 (1959).Google Scholar
  53. 51.
    Muxfeldt, H.:Synthese eines Terramycin-Bausteins. Angew. Chem.74, 825 (1962).Google Scholar
  54. 52.
    Muxfeldt, H., G. Buhr und R. Bangert: Katalytische Hydroxylierung von 12 a-Desoxy-tetracyclinen. Angew. Chem. 74, 213 (1962). Catalytic Hydroxy-lation of 12 a-Deoxy-tetracyclines. Angew. Chem. Internat. Ed. 1, 157 (1962).Google Scholar
  55. 55.
    Muxfeldt, H. und A. Kreutzer: Synthese des Desdimethylamino-anhydro-aureomycins. Chem. Ber.94, 881 (1961).CrossRefGoogle Scholar
  56. 54.
    Muxfeldt, H. und A. Kreutzer: Ab-und Aufbaureaktionen in der Anhydro-tetracyclin-Reihe. Natur-wiss. 46, 204 (1959).CrossRefGoogle Scholar
  57. 55.
    Muxfeldt, H., W. Rogalski und K. Striegler: Aufbau des Ringsystems von 6-Desoxy-tetracyclinen. Chem. Ber.95, 2581 (1962).CrossRefGoogle Scholar
  58. 56.
    Pasternack, R., L. H. Conover, A. Bavley, F. A. Hochstein, G. B. Hess and K. J. Brunings: Terramycin. III. Structure of Terracinoic Acid, an Alkaline Degradation Product. J. Amer. Chem. Soc.74, 1928 (1952).CrossRefGoogle Scholar
  59. 57.
    Perlman, D., L. J. Heuser, J. B. Semar, W. R. Frazier and J. A. Boska: Process for Biosynthesis of 7-Chloro-6-demethyltetracycline. J. Amer. Chem. Soc.83, 4481 (1961).CrossRefGoogle Scholar
  60. 58.
    Petisi, J., J. L. Spencer, J. J. Hlavka and J. H. Boothe: 6-Deoxytetracyclines. II. Nitrations and Subsequent Reactions. J. Med. Pharm. Chem.5, 538 (1962).CrossRefGoogle Scholar
  61. 59.
    Chas. Pfizer and Co., Medical Research Laboratories, Groton, Conn., Privatmitteilung.Google Scholar
  62. 60.
    Régna, P. P., I. A. Solomons, K. Murai, A. E. Timreck, K. J. Brunings and W. A. Lazier: The Isolation and General Properties of Terramycin and Terramycin Salts. J. Amer. Chem. Soc.73, 4211 (1951).CrossRefGoogle Scholar
  63. 61.
    Rennhard, H. H., R. K. Blackwood and C. R. Stephens: Fluorotetracyclines. I. Perchloryl Fluoride Studies in the Tetracycline Series. J. Amer. Chem. Soc.83, 2775 (1961).CrossRefGoogle Scholar
  64. 62.
    Schach VON Wittenau, M., J. J. Beereboom, R. K. Blackwood and C. R. Stephens: 6-Deoxytetracyclines. III. Stereochemistry at C.6. J. Amer. Chem. Soc.84, 2645 (1962).CrossRefGoogle Scholar
  65. 63.
    Scott, A. I. and C. T. Bedford: Simulation of the Biosynthesis of Tetracyclines. A Partial Synthesis of Tetracycline from Anhydroaureomycin. J. Amer. Chem. Soc.84, 2271 (1962).CrossRefGoogle Scholar
  66. 64.
    Sensi, P., G. A. DE Ferrari, G. G. GAllo und G. Rolland: 7-Bromtetra-cyclin. Farmaco (Pavia), Ed. sci.10, 337 (1955).Google Scholar
  67. 65.
    Siedel, W., F. Soeder und F. Lindner: Die Aminomethylierung der Tetracycline. Zur Chemie des Reverin®. Münchner Med. Wochenschr. 17, 661 (1958).Google Scholar
  68. 66.
    Snell, J. F., A. J. Birch and P. L. Thomson: The Biosynthesis of Tetracycline Antibiotics. J. Amer. Chem. Soc.82, 2402 (1960).CrossRefGoogle Scholar
  69. 67.
    Stephens, C. R.: Abstracts of papers, 109th Meeting Amer. Chem. Soc, Dallas, Texas, 1956, p. 18 M.Google Scholar
  70. 68.
    Stephens, C. R., L. H. Conover, P. N. Gordon, F. C. Pennington, R. L. Wagner, K. J. Brunings and F. J. Pilgrim: Epitetracycline. The Chemical Relationship between Tetracycline and “Quatrimycin”. J. Amer. Chem. Soc.78, 1515 (1956).CrossRefGoogle Scholar
  71. 69.
    Stephens, C. R., L. H. Conover, R. Pasternack, F. A. Hochstein, W. T. Moreland, P. P. Regna, F. J. Pilgrim, K. J. Brunings and R. B. Woodward: The Structure of Aureomycin. J. Amer. Chem. Soc.76, 3568 (1954).CrossRefGoogle Scholar
  72. 70.
    Stephens, C. R., K. Murai, K. J. Brunings and R. B. Woodward: Acidity Constants of the Tetracycline Antibiotics. J. Amer. Chem. Soc.78, 4155 (1956).CrossRefGoogle Scholar
  73. 71.
    Stephens, C. R., K. Murai, H. H. Rennhard, L. H. Conover and K. J. Brunings: Hydrogenolysis Studies in the Tetracycline Series. 6-Deoxytetracyclines. J. Amer. Chem. Soc.80, 5324 (1958).CrossRefGoogle Scholar
  74. 72.
    Takeuchi, Y. and M. J. Buerger: The Crystal Structure of Terramycin Hydrochloride. Proc. Nat. Acad. Sci.(USA) 46, 1366 (1960).CrossRefGoogle Scholar
  75. 72a.
    VAN Tamelen, E. E.: Structural Chemistry of Actinomycetes Antibiotics. Fortschr. Chem. organ. Naturst.16, 90 (1958).Google Scholar
  76. 73.
    Vonderbank, H.: Aureomycin und Achromycin. Arzneimittel-Forsch., 6. Beiheft, 1956.Google Scholar
  77. 74.
    Waller, C. W., B. L. Hutchings, R. W. Broschard, A. A. Goldman, W. J. Stein, C. F. WOLF and J. H. Williams: Degradation of Aureomycin. VII. Aureomycin and Anhydroaureomycin. J. Amer. Chem. Soc.74, 4981 (1952).Google Scholar
  78. 75.
    Waller, C. W., B. L. Hutchings, C. F. Wolf, R. W. Broschard, A. A. Goldman and J. H. Williams: Degradation of Aureomycin. III. 3,4-Dihydroxy-2,5-dioxocyclopentane-I-carboxamide. J. Amer. Chem. Soc.74, 4978 (1952).CrossRefGoogle Scholar
  79. 76.
    Waller, C. W., B. L. Hutchings, A. A. Goldman, C. F. Wolf, R. W. Broschard and J. H. Williams: Degradation of Aureomycin. IV. Des-dimethylaminoaureomycinic Acid. J. Amer. Chem. Soc.74, 4979 (1952).CrossRefGoogle Scholar
  80. 77.
    Waller, C. W., B. L. Hutchings, C. F. Wolf, A. A. Goldman, R. W. Broschard and J. H. Williams: Degradation of Aureomycin. VI. Isoaureo-mycin and Aureomycin. J. Amer. Chem. Soc.74, 4981 (1952).Google Scholar
  81. 78.
    Webb, J. S., R. W. Broschard, D. B. Cosulich, W. J. Stein and C. F. Wolf: Demethyltetracyclines. Structure Studies. J. Amer. Chem. Soc.79, 4563 (1957).CrossRefGoogle Scholar
  82. 79.
    Wilkinson, R. G., T. L. Fields and J. H. Boothe: Total Synthesis of Tetracyclines. III. Synthesis of a T icyclic Model System. J. Organ. Chem.(USA) 26, 637 (1961).CrossRefGoogle Scholar

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© Springer-Verlag/Wien 1963

Authors and Affiliations

  • H. Von Muxfeldt
    • 1
  • R. Bangert
    • 1
  1. 1.MadisonUSA

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