Synthesis and anti-inflammatory activity of derivatives of 5-[(2-disubstitutedamino-6-methyl-pyrimidin-4-yl)-sulfanylmethyl]-3H-1,3, 4-oxadiazole-2-thiones

Farmaco

Volumn 59, Issue 10, 2004, Pages 767-774

  Burbuliene, Milda Malvina ^a   Jakubkiene, Virginija ^a   Mekuskiene, Giedrute ^a   Udrenaite, Emilija ^a   Smicius, Romualdas ^a   Vainilavicius, Povilas ^a  

^a VILNIUS UNIVERSITY   (Lithuania)

Author keywords

3H 1,3,4 oxadiazole 2 thiones; Anti inflammatory activity

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 3 DIMETHYLAMINOMETHYL 5 [(6 METHYL 2 MORPHOLIN 4 YLPYRIMIDIN 4 YL)SULFANYLMETHYL] 3H 1,3,4 OXADIAZOLE 2 THIONE; 3 DIMETHYLAMINOMETHYL 5 [(6 METHYL 2 PIPERIDIN 1 YLPYRIMIDIN 4 YL)SULFANYLMETHYL] 3H 1,3,4 OXADIAZOLE 2 THIONE; 3 DIMETHYLAMINOMETHYL 5 [(6 METHYL 2 PYRROLIDIN 1 YLPYRIMIDIN 4 YL)SULFANYLMETHYL] 3H 1,3,4 OXADIAZOLE 2 THIONE; 5 [(6 METHYL 2 MORPHOLIN 4 YLPYRIMIDIN 4 YL)SULFANYLMETHYL] 3 (MORPHOLIN 4 YLMETHYL) 3H 1,3,4 OXADIAZOLE 2 THIONE; 5 [(6 METHYL 2 MORPHOLIN 4 YLPYRIMIDIN 4 YL)SULFANYLMETHYL] 3 (PYRROLIDIN 1 YLMETHYL) 3H 1,3,4 OXADIAZOLE 2 THIONE; 5 [(6 METHYL 2 PIPERIDIN 1 YLPYRIMIDIN 4 YL)SULFANYLMETHYL] 3 (MORPHOLIN 4 YLMETHYL) 3H 1,3,4 OXADIAZOLE 2 THIONE; 5 [(6 METHYL 2 PIPERIDIN 1 YLPYRIMIDIN 4 YL)SULFANYLMETHYL] 3 (PYRROLIDIN 1 YLMETHYL) 3H 1,3,4 OXADIAZOLE 2 THIONE; 5 [(6 METHYL 2 PYRROLIDIN 1 YLPYRIMIDIN 4 YL)SULFANYLMETHYL] 3 (MORPHOLIN 4 YLMETHYL) 3H 1,3,4 OXADIAZOLE 2 THIONE; 5 [(6 METHYL 2 PYRROLIDIN 1 YLPYRIMIDIN 4 YL)SULFANYLMETHYL] 3 (PYRROLIDIN 1 YLMETHYL) 3H 1,3,4 OXADIAZOLE 2 THIONE; ACETYLSALICYLIC ACID; ANTIINFLAMMATORY AGENT; IBUPROFEN; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; MALE; NONHUMAN; RAT;

ANIMALS; ANTI-INFLAMMATORY AGENTS; FEMALE; MALE; MICE; MICE, INBRED BALB C; OXADIAZOLES; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP; THIONES;

EID: 5044237449     PISSN: 0014827X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.farmac.2004.05.007     Document Type: Article

References (15)

1. Bettarini F., Capuzzi L., La Porta P., Massimini S., and Caprioli V. Preparation of (thi)oxadiazol- and triazol(thi)ones as miticides and insecticides 1993 EP 533276 (CA 119 (1993) 49400)
2. Pancechovska-Ksepko D., Foks H., Landowska E., Janowiec M., and Zwolska-Kwiek Z. Pyrazine derivatives. XVII. Synthesis and tuberculostatic activity of pyrazinyl-1,3,4-oxadiazole derivatives Acta Pol. Pharm. 43 1986 116 123 (Pol.) (CA 107 (1987) 198246)
3. Yamamoto S. Melanin formation-inhibiting topical preparations containing 1,3,4-oxadiazoles, 1,2,4-triazoles or 1,3,4-thiadiazoles 1993 JP 05124948 (CA 119 (1993) 146370)
4. Mulican M.D., Wilson M.W., Connor D.T., Kostlan C.R., Chrier D.J., and Dyer R.D. Design of 5-(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,4-thiadiazoles, -1,3,4-oxadiazoles and -1,2,4-triazoles as orraly active, nonulcerogenic antiinflammatory agents J. Med. Chem. 36 1993 1090 1099
5. Boschelli D.H., Connor D.T., Bornemeier D.A., Dyer R.D., Kennedy J.A., Kuipers P.J., Okonkwo G.C., Schrier D.J., and Wright C.D. 1,3,4-Oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole analogs of the fenamates n-vitro inhibition of cyclooxygenase and 5-lipoxygenase activities J. Med. Chem. 36 1993 1802 1810
6. Palaska E., Sahin G., Kelicen P., Durlu N.T., and Altinok G. Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones Farmaco 57 2002 101 108
7. Belliotti T.R., Connor D.T., and Kostlan C.R. Preparation of 2-diazolyl-4,6-di-tertiary-butyl-5-hydroxypyrimidines as cyclooxygenase and 5-lipoxygenase inhibitors 1992 WO 9213844 (CA 118 (1993) 6990)
8. Saxena S., Verma M., Saxena A.K., and Shanker K. 1,3,4-Oxadiazolethiones as inflammation inhibitors Indian J. Pharm. Sci. 54 1992 1 3
9. Eckhardt W., Beriger E., and Zondler H. Preparation of 2-mercapto-5-pyrimidinyl-1,3,4-oxadiazoles with nematocidal and fungicidal activity 1990 EP 371925 (CA 113 (1990) 191385)
10. Mekuskiene G., Vainilavicius P., Hetzheim A., and Sematovic R. Synthesis of 5-(4,6-dimethyl-2-pyrimidinyl)-1,3,4-oxadiazole-2-thione Khim. Geterotsikl. Soedin. 1993 700 705 (Russ.) (CA 120 (1994) 8554)
11. Burbuliene M.M., Udrenaite E., Gaidelis P., and Vainilavicius P. Reactions of 5-(2-dimethylamino-6-methyl-4-pyrimidinylsulfanylmethyl)-1,3,4- oxadiazole-2-thione with carbon electrophiles Polish J. Chem. 76 2002 557 563
12. Jakubkiene V., Burbuliene M.M., Mekuskiene G., Udrenaite E., Gaidelis P., and Vainilavicius P. Synthesis and anti-inflammatory activity of 5-(6-methyl-2-substituted 4-pyrimidinyloxymethyl)-1,3,4-oxadiazole-2-thiones and their 3-morpholinomethyl derivatives Il Farmaco 58 2003 323 328
13. Winter C.A., Risley E.A., and Nuss G.W. Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs Proc. Soc. Exp. Biol. Med. 111 1962 544 547
14. Marek J. Bentonite-induced rat paw oedema as a tool for simultaneous testing of prophylactic and terapeutic effects of anti-inflammatory and other drugs Pharmazie 36 1981 46 49
15. Litchfield J.T., and Wilkoxon F.J. A simplified method of evaluating dose-effect experiments Pharmacol. Exp. Ther. 96 1949 99 105