Synthesis and Biological Investigations of New Thiazolidinone and Oxadiazoline Coumarin Derivatives

  • 발행 : 2003.09.01

초록

Ethyl (coumarin-4-oxy)acetate 1 was prepared through the reaction of 4-hydroxycoumarin with ethyl bromoacetate. Compound 1 was allowed to react with hydrazine hydrate to produce coumarin-4-oxyacetic hydrazide 2. The synthesis of N-(arylidene and alkylidene)-coumarin-4-oxyacetic hydrazones 3-20 was performed. The preparation of 2-substituted-3-[(coumarin-4-oxy) acetamido]thiazolidinones 21-26 and 2-[(coumarin-4-oxy )methyl]-4-acetyl-5-substituted-$\Delta^2$-1,3,4-oxadiazolines 27-33 was performed by the reaction of the hydrazones 3, 4, 7, 9, 12, 14 with mercaptoacetic acid and the hydrazones 3, 4, 5, 7, 12, 15, 16 with acetic anhydride, respectively. The antiviral activities, cytotoxicities and structure-activity relationship (SAR) towards different microorganisms of the prepared compounds were studied.

키워드

참고문헌

  1. Abbas, S. E., El-Ansary, S. L., and Mikhael, A. N., Synthesis of some 1,3,4 -oxadiazolines and thiazolidinones of expected antibacterial activity. Egypt. J. Pharm. Sci., 35(1-6), 21-30 (1994)
  2. Abde-Hamid, A. Z. and Fathalla, O. A., Effect of some new uracil derivatives on Ehrlich ascites carcinoma cells. Egypt. J. Pharm. Sci., 34(1-3), 67-80 (1993)
  3. Arora, R. B. and Mathur, C. N., Relationship between structure and anticoagulant activity of coumarin derivatives. Brit. J. Pharmacol., 20, 29-35 (1963)
  4. Chemielewska, I. and Cieslak, J., Vitamins and antivitamin K. Tautomerism of dicoumarol. Tetrahedron, 4,135-146 (1958) https://doi.org/10.1016/0040-4020(58)88012-6
  5. Choubey, V. N. and Singh, H., Synthesis of fungistatic thiazolidinones. Bull. Chem. Soc. Japan 43(7), 2233-2236 (1970); C.A., 73, 77120d (1970) https://doi.org/10.1246/bcsj.43.2233
  6. Dalla Via, L., Gia, O., Marciani Magno, S., Santana, L.,Teijeira, M., and Uriarte, E., New tetracyclic analogues of photochemotherapeutic drugs 5-MOP and 8-MOP: synthesis, DNA interaction, and antiproliferative activity. J. Med. Chem., 42(21), 4405-4413 (1999) https://doi.org/10.1021/jm9910829
  7. Egorov, N. S., 'Antibiotics: A Scientific Approach', Mir Publisher, Moscow, (1985)
  8. El-Bendary, E. R. and Badria, F. A., Synthesis, DNA-binding and antiviral activity of certain pyrazolo[3,4 - d]pyrimidine derivatives. Arch. Pharm. Med. Chem., 333(4), 99-103 (2000) https://doi.org/10.1002/(SICI)1521-4184(20004)333:4<99::AID-ARDP99>3.0.CO;2-O
  9. El-Sherbeny, M. A., Badria, F. A., and Kheira, S. A., Synthesis of some new[4,5-d]pyrimidine derivatives and evaluation of their antifungal, antiviral and cytotoxic activities. Med. Chem. Res., 6, 28-39 (1996)
  10. El-Sherbeny, M. A., El-Ashmawy, M. B., El-Subbagh, H. I., El-Emam, A. A., and Badria, F. A., Synthesis, antimicrobial and antiviral evaluation of certain thienopyrimidine derivatives. Europ. J. Med. Chem., 30, 445-449 (1995) https://doi.org/10.1016/0223-5234(96)88255-9
  11. El-Subbagh, H. I., Abu-Zaid, S. M., Mahran, M. A., Badria, F. A., and Al-obaid, A. M., Synthesis and biological evaluation of certain alpha, beta- unsaturated ketones and their corresponding fused pyridines as antiviral and cytotoxic agents. J. Med. Chem., 43(15), 2915-2921 (2000) https://doi.org/10.1021/jm000038m
  12. El-Subbagh, H. I., El-Nagar, W. A., and Badria, F. A., Synthesis and biological testing of certain thiazole derivatives as potential cytotoxic agents. Sci. Pharm., 62, 237-245 (1994)
  13. El-Subbagh, H. I., El-Sherbeny, M. A., Nasr, M. N., Goda, F. E., and Badria, F. A., Novel diarylsulphide derivatives as potential cytotoxic agents. Bull. Chim. Faraceutico, 134(2), 80-84 (1995)
  14. Erbring, V. H., Uebel, H., and Vogel, G., Zur chemie, pharmakologie und toxikologie von visnadin. Arzneim. Forsch., 17, 283-287 (1967)
  15. Fathy, N. M., Abdel-Motti, F., and Abdel-Megeid, F. M. E., Synthesis of some thienoquinoline derivatives with expected pharmacological activity. Egypt. J. Pharm. Sci., 31(1-4), 375 - 383 (1990); C.A. 114, 101767h (1991)
  16. Hufford, C. D., Badria, F. A., Abou-Karam, M. Shier, W. T., and Rogers, R. D., Preparation, characterization and antiviral activity of microbial metabolites of stemodin. J. Nat. Prod., 54(6), 1543 (1991) https://doi.org/10.1021/np50078a008
  17. Kamdar, G. C., Chavda, A. C., and Parikh, A. R., Preparation and antibacterial activity of 2-phenyl-3-(2',4'- diarylamino-striazin-6-yl)-5/H/$CH_3$-carboxymethyl-4-thiazolidinone and 2-aryl-3-(p-aminosulphophenyl/2'-pyrimidylaminosulphophenyl)-p-carboxymethyl-4-thiazolidinones. J. Indian Chem. Soc., 64 (5), 298-301 (1987)
  18. Matsumoto, A. and Hanawalt, P. C., Histone H3 and heat shock protein GRP78 are selectively cross-linked to DNA by photoactivated gilvocarcin V in human fibroblasts. Cancer Res., 60(14), 3921-3926 (2000)
  19. Meher, S. S., Naik, S., Behera, R. K., and Nayak, A., Studies on thiazolidinones. Part XI: Synthesis and fungitoxicities of thiazolidinones, thiohydantoins and their derivatives derived from thiosemicarbazones. J. Indian Chem. Soc., 58(3), 274-276 (1981)
  20. Nagesam, M., Raju, K. M., and Raju, M.S., Synthesis and antibacterial activity of 4,6-dimethyl-3-substituted aminomethylcoumarins. Chim. Acta Turc., 17(2), 255-262 (1989); C.A. 114, 61883j (1991)
  21. Popp, F. D., Synthesis of potential anticancer agents. II. Some schiff bases. J. Org. Chem. 26, 1566-1568 (1961) https://doi.org/10.1021/jo01064a063
  22. Rao, V. R., Rao, T. V. P., Rao, B. R., and Reddy, Y. D., Studies on coumarin derivatives. Part III. Synthesis and biological activity of some 2-[aryl/heteroarylcarbonylmethylthio]-6-methyl-8H-pyrano[2,3-e]benzoxazol-8-one. Ind. J. Chem., sect. B, 25B(3), 332-333 (1986); C.A. 106, 84453t (1987)
  23. Sagitullin, R. S. and Kost, A. N., Reactions of the hydrazine derivatives. XXV. Action of acetic anhydride and polyphosphoric acid on acylhydrazones. Vestnik Moskov. Univ., Ser. Mat., Mekh., Astron., Fiz. I Khim., 14(4), 187-193 (1959); cf. C.A. 53, 21894d (1959); C.A. 54, 14553c (1960)
  24. Selleri, R., Orzalesi, G., Caldini, O., and Spano, R., New coumarin derivatives with saluretic and choleretic activity. Arzneim. Forsch., 16, 1073 (1966)
  25. Seo, E. K., Chai, H. B., Chagwedera, T. E., Farnsworth, N. R., Cordell, G. A., Pezzuto, J. M., and Kinghorn, A D., 5-(4-Hydroxyphenthenyl)-4,7-dimethoxycoumarin, a new constituent of Monotes engleri. Planta Med., 66(2), 182-184 (2000) https://doi.org/10.1055/s-0029-1243128
  26. Singh, R., Singh, R. P., Malik, Om. P., and Makarandi, J. K., Synthesis and antifungal activity of some alkylsubstituted 4-(substituted phenoxymethyl)-2H-1-benzopyran-2-one. Ind. J. Chem., sect. B, 28B(11), 996-998 (1989); C.A.112, 178571f (1990)
  27. Smith, E., Hosansky, N., Bywater,W.G., and Tamelen, E.E.V., Constitution of samidin, dihydrosamidin and visnadin. J. Am. Chem. Soc., 79, 3534-3540 (1957) https://doi.org/10.1021/ja01570a062
  28. Valenti, P., Rampa, A., Recanatini, M., Bisi, A., Belluti, F., Da Re, P., Carrara, M., and Cima, L., Synthesis, cytotoxicity and SAR of simple geiparvarin analogues. Anticancer Drug Des., 12(6), 443-451 (1997)
  29. Weber, U. S., Steffen, B., and Siegers, C. P., Antitumor-activities of coumarin, 7-hydroxycoumarin and its glucuronide in several human tumor cell lines. Res. Commun. Mol. Pathol. Pharmacol., 99(2), 193-206 (1998)