Abstract
Enol lactones such as 4-hydroxy-6-methyl-2H-pyran-2-one (triacetic acid lactone, TAL) and 4-hydroxycoumarin when treated with 2-amino-3-formylchromone under basic conditions afforded 3-acetoacetyl benzopyranopyridones and benzopyranopyridines, respectively. A series of pyrazole derivatives was prepared by the reaction of 3-acetoacetyl benzopyranopyridones with different hydrazines. All compounds were characterised on the basis of spectral data and their antibacterial activity evaluated.
Similar content being viewed by others
References
Aqil, F., & Ahmad, I. (2003). Broad-spectrum antibacterial and antifungal properties of certain traditionally used Indian medicinal plants. World Journal of Microbiology and Biotechnology, 19, 653–657. DOI: 10.1023/A:1025128104056.
Ashwood, V. A., Buckingham, R. E., Cassidy, F., Evans, J.M., Faruk, E. A., Hamilton, T. C., Nash, D. J., Stemp, G., & Willcocks, K. (1986). Synthesis and antihypertensive activity of 4-(cyclic amido)-2H-1-benzopyrans. Journal of Medicinal Chemistry, 29, 2194–2201. DOI: 10.1021/jm00161a011.
Ashwood, V. A., Cassidy, F., Evans, J. M., Gagliardi, S., & Stemp, G. (1991). Synthesis and antihypertensive activity of pyran oxygen and amide nitrogen replacement analogs of the potassium channel activator cromakalim. Journal of Medicinal Chemistry, 34, 3261–3267. DOI: 10.1021/jm00115a015.
Bailey, D. M., Hansen, P. E., Hlavac, A. G., Baizman, E. R., Pearl, J., DeFelice, A. F., & Feigenson, M. E. (1985). 3,4-Diphenyl-1H-pyrazole-1-propanamine antidepressants. Journal of Medicinal Chemistry, 28, 256–260. DOI: 10.1021/jm00380a020.
Bauer, A. W., Kirby, W. M. M., Sherris, J. C., & Turck, M. (1966). Antibiotic susceptibility testing by a standardized single disk method. American Journal of Clinical Pathology, 45, 493–496.
Bergmann, R., & Gericke, R. (1990). Synthesis and antihypertensive activity of 4-(1,2-dihydro-2-oxo-l-pyridyl)-2H-l-benzopyrans and related compounds, new potassium channel activators. Journal of Medicinal Chemistry, 33, 492–504. DOI: 10.1021/jm00164a005.
Borroni, E. M, Huber-Trottmann, G., Kilpatrick, G. J., & Norcross, R. D. (2001). World patent No. 062233. Geneva, Switzerland: World Intellectual Property Organization.
Busev, A. I., Akimov, V. K., & Gusev, S. I. (1965). Pyrazolone derivatives as analytical reagents. Russian Chemical Reviews, 34, 237–249. DOI: 10.1070/Rc1965v034n03ABEH001426.
Butt, M. A., & Elvidge, J. A. (1963). Heterocyclic synthesis with malonyl chloride. Part VIII. Hydroxypyrones from 1,3-diketones. Journal of Chemical Society, 1963, 4483–4489. DOI: 10.1039/JR9630004483.
Cechetti, V., Tabarrini, O., & Sabatini, S. (2006). From cromakalim to different structural classes of KATP channel openers. Current Topics In Medicinal Chemistry, 6, 1049–1068. DOI: 10.2174/156802606777323683.
Cervello, J., Gil, M., de March, P., Marquet, J., Moreno-Mañas, M., Roca, J. L., & Sanchez-Ferrando, F. (1987). Use of selective heteronuclear 13C1H noe measurements. A second note of warning on the assignment of structure to the products formed in the reactions between 4-hydroxy-2H-pyran-2-ones and carbonyl compounds. Tetrahedron, 43, 2381–2387. DOI: 10.1016/s0040-4020(01)86824-1.
Chauhan, P. M. S., Singh, S., & Chatterjee, R. K. (1993). Antifungal profile of substituted pyrazoles: A new class of antifilarial agents. Indian Journal of Chemistry Sect B, 32, 858–861.
Connor, D. T., Unangst, P. C., Schwender, C. F., Sorenson, R. J., Carethers, M. E., Puchalski, C., & Brown, R. E. (1984). Synthesis of 1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c] pyridin-5-ones. II. Substitution at the 3-position with 2-aminoethyl and 2-aminopropyl side chains. Journal of Heterocyclic Chemistry, 21, 1561.1564. DOI: 10.1002/jhet.5570 210564.
Dardari, Z., Lemrani, M., Sebban, A., Bahloul, A., Hassar, M., Kitane, S., Berrada, M., & Boudouma, M. (2006). Antileishmanial and antibacterial activity of a new pyrazole derivative designated 4-[2-(1-(ethylamino)-2-methyl-propyl)phenyl]-3-(4-methyphenyl)-1-phenylpyrazole. Archiv der Pharmazie, 339, 291–298. DOI: 10.1002/ardp.200500266.
de March, P., Moreno-Mañas, M., & Roca, J. L. (1984). The reactions of 4-hydroxy-2-pyrones with 2-hydroxybenzaldehydes. A note of warning. Journal Of Heterocyclic Chemistry, 21, 1371–1372. DOI: 10.1002/jhet.1984.5570210525.
Ellis, G. P. (1977). General methods of preparing chromones. In G. P. Ellis (Ed.), Chemistry of heterocyclic compounds: Chromenes, chromanones, and chromones, (Vol. 31, pp. 526–527). New York, NY, USA: Wiley. DOI: 10.1002/9780470187012.ch9.
El-Subbagh, H. I., Abu-Zaid, S. M., Mahran, M. A., Badaria, F. A., & Al-Obaid, A. M. (2000). Synthesis and biological evaluation of certain α, β-unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents. Journal of Medicinal Chemistry, 43, 2915–2921. DOI: 10.1021/jm000038m.
Evdokimov, N. M., Kireev, A. S., Yakovenko, A. A., Antipin, M. Yu., Magedov, I. V., & Kornienko, A. (2006). Convenient one-step synthesis of a medicinally relevant benzopyranopyridine system. Tetrahedron Letters, 47, 9309–9312. DOI: 10.1016/j.tetlet.2006.10.110.
Garcia, H., Iborra, S., Miranda, M. A., Morera, I. M., & Primo, J. (1991). Pyrazoles and isoxazoles derived from 2-hydroxyaryl phenylethynyl ketones: Synthesis and spectrophotometric evaluation of their potential applicability as sunscreens. Heterocycles, 32, 1745–1755. DOI: 10.3987/COM-91-5773.
Hagen, H., Nilz, G., Walter, G., & Landes, A. (1992). German PatentNo. 4,039,272. Munich, Germany: German Patent and Trade Mark Office.
Hosni, H. M., & Abdulla, M. M. (2008). Anti-inflammatory and analgesic activities of some newly synthesized pyridinedicarbonitrile and benzopyranopyridine derivatives. Acta Pharmaceutica, 58, 175–186. DOI: 10.2478/v10007-008-0005-4.
Katritzky, A. R., & Rees, C. W. (1984). Comprehensive heterocyclic chemistry. New York, NY, USA: Pergamon press.
Lee, S.-K., Chae, S.-M., Yi, K.-Y., Kim, N.-J., & Oh, C.-H. (2005). 4-[(N-Imidazol-2-ylmethyl)anilino]pyranopyridine analogs as novel anti-angiogenic agents. Bulletin of Korean Chemical Society, 26, 619–628. DOI: 10.5012/bkcs.2005.26.4. 619.
Nohara, A., Ishiguro, T., Ukawa, K., Sugihara, H., Maki, Y., & Sanno, Y. (1985). Studies on antianaphylactic agents. 7. Synthesis of antiallergic 5-oxo-5H-[1]benzopyrano[2,3-b]pyridines. Journal of Medicinal Chemistry, 28, 559–568. DOI: 10.1021/jm50001a005.
Paciorek, P. M., Burden, D. T., Burke, Y. M., Cowlrick, I. S., Perkins, R. S., Taylor, J. C., & Waterfall, J. F. (1990). Preclinical pharmacology of Ro 31-6930, a new potassium channel opener. Journal of Cardiovascular Pharmacology, 15, 188–192.
Patel, M. V., Bell, R., Majest, S., Henry, R., & Kolasa, T. (2004). Synthesis of 4,5-diaryl-1H-pyrazole-3-ol derivatives as potential COX-2 inhibitors. The Journal of Organic Chemistry, 69, 7058–7065. DOI: 10.1021/jo049264k.
Petersen, U., & Heitzer, H. (1976). Reaktionen mit 4-oxo-4H-chromen-3-carbaldehyd, I herstellung und reaktionen von 2-amino-4-oxo-4H-chromen-3-carbaldehyd. Justus Liebigs Annalen der Chemie, 9, 1659–1662. DOI: 10.1002/jlac.1976197 60913.
Prokopp, C. R., Rubin, M. A., Sauzem, P. D., de Souza, A. H., Berlese, D. B., Lourega, R. V., Muniz, M. N., Bonacorso, H. G., Zanatta, N., Martins, M. A. P., & Mello, C. F. (2006). A pyrazolyl-thiazole derivative causes antinociception in mice. Brazilian Journal of Medical and Biological Research, 39, 795–799. DOI: 10.1590/S0100-879X2006000600013.
Schurreit T. (1987). 4-Hydroxy-2H-[1]benzopyran-2-on als Baustein zur Synthese von Bisbenzopyranopyridinen. Archiv der Pharmazie, 320, 500–506. DOI: 10.1002/ardp.19873200605.
Sethna, S. M., & Shah, N. M. (1945). The chemistry of coumarins. Chemical Reviews, 36, 1–62. DOI: 10.1021/cr601 13a001.
Shchegol’kov, E. V., Khudina, O. G., Anikina, L. V., Burgart, Ya. V., & Saloutin, V. I. (2006). Synthesis, analgesic and antipyretic activity of 2-(antipyrin-4-yl)hydrazones of 1,2,3-triketones and their derivatives. Pharmaceutical Chemistry Journal, 40, 373–376. DOI: 10.1007/s11094-006-0130-7.
Siddiqui, Z. N., & Asad, M. (2006). New heterocyclic derivatives of 3-formyl-4-hydroxycoumarin. Indian Journal of Chemistry, 45B, 2704–2709.
Siddiqui, Z. N., Khuwaja, G., & Asad, M. (2006). One pot synthesis of 3-acetoacetyl-5-oxo-5H-[1] benzopyrano [3,2-e]pyridin-2-one from triacetic acid lactone. Indian Journal of Chemistry, 45B, 2341–2345.
Singh, P., Paul, K., & Holzer, W. (2006). Synthesis of pyrazolebased hybrid molecules: Search for potent multidrug resistance modulators. Bioorganic & Medicinal Chemistry, 14, 5061–5071. DOI: 10.1016/j.bmc.2006.02.046.
Singh, S. P., Sehgal, S., Tarar, L. S., & Dhawan, S. N. (1990). Synthesis of 2-[3-methyl or trifluromethyl-5-(2-thienyl)-pyrazol-1-yl]thiazol and benzothiazoles. Indian Journal of Chemistry, 29B, 310–314.
Srivastava, S. K., Tripathi, R. P., & Ramachandran, R. J. (2005). NAD+-dependent DNA ligase (Rv3014c) from mycobacterium tuberculosis. Crystal structure of the adenylation domain and identification of novel inhibitors. The Journal of Biological Chemistry, 280, 30273–30281. DOI: 10.1074/jbc.M503780200.
Sullvian, W. R., Huebner, C. F., Stahmann, M. A., & Link, K. P. (1943). Studies on 4-hydroxycoumarins. II. The condensation of aldehydes with 4-hydroxycoumarins. Journal of the American Chemical Society, 65, 2288–2291. DOI: 10.1021/ja01252a008.
Schurreit T. (1987). 4-Hydroxy-2H-[1]benzopyran-2-on als Baustein zur Synthese von Bisbenzopyranopyridinen. Archiv der Pharmazie, 320, 500–506. DOI: 10.1002/ardp.19873200605.
Unangst, P. C., Capiris, T., Connor, D. T., Heffner, T. G., MacKenzie, R. G., Miller, S. R., Pugsley, T. A., & Wise, L. D. (1997). Chromeno[3,4-c]pyridin-5-ones: Selective human dopamine D4 receptor antagonists as potential antipsychotic agents. Journal of Medicinal Chemistry, 40, 2688–2693. DOI: 10.1021/jm970170v.
Vicentini, C. B., Guccione, S., Giurato, L., Ciaccio, R., Mares, D., & Forlani, G. J. (2005). Pyrazole derivatives as photosynthetic electron transport inhibitors: New leads and structure-activity relationship. Journal of Agricultural and Food Chemistry, 53, 3848–3855. DOI: 10.1021/jf0500029.
Vors, J.-P., Gerbaud, V., Gabas, N., Canselier, J. P., Jagerovic, N., Jimeno, M. L., & Elguero, J. (2003). The structure of the agrochemical fungicidal 4-chloro-3-(3,5-dichlorophenyl)-1H-pyrazole (RPA 406194) and related compounds. Tetrahedron, 59, 555–560. DOI: 10.1016/s0040-4020(02)01487-4.
Wardakhan, W. W., & Louca, N. A. (2007). Synthesis of novel pyrazole, coumarin and pyridazine derivatives evaluated as potential antimicrobial and antifungal agents Journal of the Chilean Chemical Society, 52, 1145–1149. DOI: 10.4067/S0717-97072007000200006.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Siddiqui, Z.N., Praveen, S. & Farooq, F. Novel benzopyranopyridine derivatives of 2-amino-3-formylchromone. Chem. Pap. 64, 818–824 (2010). https://doi.org/10.2478/s11696-010-0072-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11696-010-0072-0