Synthesis and in vitro evaluation of some novel benzofuran derivatives as potential anti-HIV-1, anticancer, and antimicrobial agents

• Published in: Archives of pharmacal research Vol. 29; no. 1; pp. 16 - 25
• Main Authors: Rida, Samia M, El-Hawash, Soad A M, Fahmy, Hesham T Y, Hazza, Aly A, El-Meligy, Mostafa M M
• Format: Journal Article
• Language: English
• Published: Korea (South) 01.01.2006
• Subjects: Anti-HIV Agents - chemical synthesis; Anti-HIV Agents - pharmacology; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - pharmacology; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - pharmacology; Bacteria - drug effects; Benzofurans - chemical synthesis; Benzofurans - pharmacology; CD4-Positive T-Lymphocytes - virology; Cell Line, Tumor; Cyclization; Drug Evaluation, Preclinical; HIV-1 - drug effects; Humans; Indicators and Reagents; Microbial Sensitivity Tests; Models, Molecular
• ISSN: 0253-6269
• DOI: 10.1007/BF02977463

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 [symbols, see text] the viral cytopathic effect (93.19% and 59.55%) at concentrations > 2.0 x 10(-4) M and 2.5 x 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.