E-ISSN: 2148-6247
SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME 3,5-DISUBSTITUTED-TETRAHYDRO-2H-1,3,5-THIADIAZINE-2-THIONE DERIVATIVES
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Original Article
VOLUME: 8 ISSUE: 2
P: 159-168
August 2011

SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME 3,5-DISUBSTITUTED-TETRAHYDRO-2H-1,3,5-THIADIAZINE-2-THIONE DERIVATIVES

Turk J Pharm Sci 2011;8(2):159-168
Evren SAĞLAM 1
Selma SARAÇ 1
Mevlüt ERTAN 1
Ekrem KILIÇ 2
Meral ÖZALP 2
1. Hacettepe University, Faculty Of Pharmacy, Department Of Pharmaceutical Chemistry, 06100 Ankara, Turkey
2. Hacettepe University, Faculty Of Pharmacy, Department Of Pharmaceutical Microbiology, 06100 Ankara, Turkey
No information available.
No information available
Received Date: 21.07.2010
Accepted Date: 03.09.2010
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ABSTRACT

A series of new 3,5-disubstituted-tetrahydro-2H-l,3,5-thiadiazine-2-thione (THTT) derivatives (4a-g) were prepared using a convenient and general one-pot procedure and evaluated for their in vitro antibacterial and antifungal activities by using the microdilution method in comparison with ampicillin and fluconazole. 3-Phenyl-5-(l-phenylethyl)-tetrahydro-2H-l,3,5-thiadiazine-2-thione (4a) and 3-phenyl-5-hydroxy-tetrahydro-2H-l,3,5-thiadiazine-2-thione (4g) were found to be active against Staphylococcus aureus and Enterococcus faecalis with MIC values of 4 and 16 ug/mL, respectively. The antifungal activity of 3-phenyl-5-(l-phenylethyl)-tetrahydro-2H-l,3,5-thiadiazine-2-thione (4a) against Candida krusei and C. parapsilosis appeared greater than that of fluconazole (MIC: 64 ug/mL and 8 ug/mL) with MIC of 8 and 4 fig/mL, respectively. 3-Phenyl-5-(l-phenylethyl)-tetrahydro-2H-l,3,5-thiadiazine-2-thione (4a) also exhibited antifungal activity against C. albicans with a MIC of 4 jug/mL. The antifungal activity of 3-(l-phenylethyl-5-[a-(isobutyl)carboxymethyl]-tetrahydro-2H-l,3,5-thiadiazine-2-thione (4b) and 3-benzyl-5-carboxyethyl-tetrahydro-2H-l,3,5-thiadiazine-2-thione (4c) against C. krusei were found to be similar to that offluconazole (MIC: 64 ug/mL).