Synthesis of some 4-phenyl/cyclohexyl-5-(1-phenoxyethyl)-2,4-dihydro-3H-1,2,4-triazol-3-thione derivatives and their antifungal, antibacterial activities

ABSTRACT PhD. Thesis SYNTHESIS OF SOME 4-PHENYL/CYCLOHEXYL-5- (l-PHENOXYETHYL)-2,4-DIHYDRO-3H-l,2,4-TRIAZOL-3-THIONE DERIVATIVES AND THEIR ANTIFUNGAL, ANTIBACTERIAL ACTIVITIES Zafer Asım KAPLANCIKLI Anadolu University Institute of Health Sciences Department of Pharmaceutical Chemistry Supervisor: Prof. Dr. Gülhan TURAN 2003 The literature research about 4,5-disubstituted-2,4-dihydro-3H- 1,2,4- triazol-3-thione derivatives show that these compounds have antifungal and antibacterial activities. The aim of this study is to obtain 4-phenyl/cyclohexyl-5-(l-phenoxyethyl)- 3-[N-(2'-thiazolyl)acetamido]thio-4H-l,2,4-triazole derivatives. mIn order to obtain the compounds aimed, three different 2-chloro-N-(2- thiazolyl)acetamide derivatives and 5 different 4-phenyl/cyclohexyl-5-(l- phenoxyethyl)-2,4-dihydro-3H-l,2,4-triazol-3-thione derivates, two of which reported for the first time, were synthesized as starting compounds in two groups. Preperation of the novel fifteen 4-phenyl/cyclohexyl-5-(l-phenoxyethyl)- 3-[N-(2'-thiazolyl)acetamido]thio-4H-l,2,4-triazole derivatives have been accomplished by the nucleophilic substitution reaction between these two group of starting materials. Physichal properties, Rf values on thin layer chromatography, Rt values on high pressure liquid chromatography, UV absorption properties of the compounds have been determined and their structure has been elucidated by IR, 'H-NMR, MS spectra and elemental analyses. Promising results have been obtained from the in-vitro antifungal and antibacterial activities of twenty compounds which include some of the starting and resulted materials. Key Words: 1,2,4-triazole, thiazole, antifungal activity, antibacterial activity IV