SYNTHESIS OF 2-TRIFLUOROMETHYL-4,7-DIHYDRO-7- OXO-(1,2,4)TRIAZOLO[1,5-a]PYRIMIDINE-6-CARBOXYLIC ACID DERIVATIVES AS POTENTIAL ANTIMYCOBACTERIAL AND ANTIMICROBIAL AGENTS | ||||
| Bulletin of Pharmaceutical Sciences Assiut University | ||||
| Article 7, Volume 31, Issue 1, June 2008, Page 109-121 PDF (233.38 K) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/bfsa.2008.64214 | ||||
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| Author | ||||
| Nawal A. El-Koussi | ||||
| Department of Medicinal Chemistry, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt | ||||
| Abstract | ||||
| Syntheses of the target compounds were achieved by reaction of 3-amino-5-trifluoromethyl-1,2,4-triazole 1 and diethylethoxymethylenemalonate (DEEM) in glacial acetic acid to afford ethyl 2-(trifluoromethyl)-4,7-dihydro-7-oxo[1,2,4]-triazolo[1,5- a]pyrimidine-6-carboxylate 2. Reaction of compound 2 with hydroxylamine hydrochloride gave hydroxamic acid 3, while reaction with hydrazine hydrate in methanol gave the corresponding carbohydrazide 4. Schiff bases of compound 4 with appropriate aldehyde yielded series 5a-g. Refluxing of hydrazide 4 with appropriate isothiocyanate gave thiosemicarbazides 6a-f. The antimycobacterial evaluation was determined against Mycobacterium tuberculosis H37Rv(ATCC 27294). Compound 5e and 5b showed activity with IC90(6.672, 7.362 μg/ml respectively) and IC50 (4.627, 6.382 μg/ml respectively). In vitro antibacterial screening for the prepared compounds were determined against certain strains of gram positive and gram negative bacteria. The results showed that compounds 3, 5a, 6b possessed higher activity than ampicillin against all strains, also the activity range from half to sixth activity of nalidixic acid against E. coli. Compounds 3, 5a, 5b, 5c, 5f, 6b exhibited activity against P. aeruginosa, while nalidixic acid possessed no activity. Compounds 3, 5a, 5b and 6b possessed antifungal activity. | ||||
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