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Synthesis and In Vitro Evaluation of Some Novel Benzofuran Derivatives as Potential Anti-HIV-1, Anticancer, and Antimicrobial Agents  

Rida, Samia M. (Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Alexandria)
EI-Hawash, Soad A.M. (Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Alexandria)
Fahmy, Hesham T.Y. (Department of Pharmaceutical Sciences, College of Pharmacy, South Dakota State University)
Hazza, Aly A. (Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Alexandria)
EI-Meligy, Mostafa M.M. (Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Alexandria)
Publication Information
Archives of Pharmacal Research / v.29, no.1, 2006 , pp. 16-25 More about this Journal
Abstract
A novel series of 1-(1-benzofuran-2-yl-ethylidene)-4-substituted thiosemicarbazides (2a-d) along with some derived ring systems: substituted-2,3-dihydro-thiazoles(3a-c, 4a-f) and thiazolidin-4-ones(5a-d and 6a-d), were synthesized. In addition, cyanoacetic acid-(1-benzofuran-2-yl-ethylidene) hydrazide(7) was used to prepare another new series of compounds consisting of substituted pyridin-2(1H)-ones(8a-c); 2-thioxo-2,3-dihydro-thiazoles(9a-d) and 2-thioxo-2,3-dihydro-6H-thiazolo[4,5-d]pyrimidin-7-ones (10a-c, 11a-c). The absolute configuration of compound 5c was determined by X-ray crystallography. The compounds prepared were evaluated for their in vitro anti-HIV, anticancer, antibacterial, and antifungal activities. Among the tested compounds, compounds 5c and 9a produced a significant reduction ㅐ ㄹ the viral cytopathic effect (93.19% and 59.55%) at concentrations $>2.0{\times}10^{-4}\;M\;and\;2.5{\times}10^{-5}\;M$respectively. Compound 9a was confirmed to have moderate anti-HIV activity. Compounds 2a, 2d, and 5c showed mild antifungal activity. However, none of the tested compounds showed any significant anticancer activity.
Keywords
2-Acetylbenzofuran; Thiosemicarbazides; Caynoacetic acid hydrazide; Dihydro-thiazole; Pyridin-2(1H)-ones; Thiazolo[4,5-d]pyrimidines; Anti-HIV-1; Anticancer; Antimicrobial activity;
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