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Synthesis and Biological Investigations of New Thiazolidinone and Oxadiazoline Coumarin Derivatives  

Abd Elhafez, Omaima Mohamed (Chemistry of Natural and Microbial Products Department, National Research Centre)
El Khrisy, Ezz El Din Ahmed Mohamed (Chemistry of Natural and Microbial Products Department, National Research Centre)
Badria, Farid (Pharmacognosy Department, Faculty of Pharmacy, Mansoura University)
Fathy, Alaa El Din Mohamed (Chemistry of Natural and Microbial Products Department, National Research Centre)
Publication Information
Archives of Pharmacal Research / v.26, no.9, 2003 , pp. 686-696 More about this Journal
Abstract
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.
Keywords
4-Hydroxycoumarin; Ethyl (coumarin-4-oxy)-acetate; Coumarin-4-oxyacetic hydrazide; Hydrazones; Thiazolidinones; Oxadiazolines; Antiviral; Cytotoxicity; Structure-activity relationship;
Citations & Related Records

Times Cited By Web Of Science : 9  (Related Records In Web of Science)
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1 Arora, R. B. and Mathur, C. N., Relationship between structure and anticoagulant activity of coumarin derivatives. Brit. J. Pharmacol., 20, 29-35 (1963)
2 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)   DOI   ScienceOn
3 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)   DOI   ScienceOn
4 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)   DOI   ScienceOn
5 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)
6 Popp, F. D., Synthesis of potential anticancer agents. II. Some schiff bases. J. Org. Chem. 26, 1566-1568 (1961)   DOI
7 Selleri, R., Orzalesi, G., Caldini, O., and Spano, R., New coumarin derivatives with saluretic and choleretic activity. Arzneim. Forsch., 16, 1073 (1966)
8 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)   PUBMED
9 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)   PUBMED
10 Choubey, V. N. and Singh, H., Synthesis of fungistatic thiazolidinones. Bull. Chem. Soc. Japan 43(7), 2233-2236 (1970); C.A., 73, 77120d (1970)   DOI   ScienceOn
11 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)
12 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)
13 Erbring, V. H., Uebel, H., and Vogel, G., Zur chemie, pharmakologie und toxikologie von visnadin. Arzneim. Forsch., 17, 283-287 (1967)
14 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)   PUBMED
15 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)   DOI   ScienceOn
16 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)
17 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)
18 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)
19 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)
20 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)
21 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)
22 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)   DOI
23 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)
24 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)   DOI   PUBMED
25 Egorov, N. S., 'Antibiotics: A Scientific Approach', Mir Publisher, Moscow, (1985)
26 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)   DOI   PUBMED
27 Chemielewska, I. and Cieslak, J., Vitamins and antivitamin K. Tautomerism of dicoumarol. Tetrahedron, 4,135-146 (1958)   DOI   ScienceOn
28 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)
29 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)