Synthesis and in vitro evaluation of some novel benzofuran derivatives as potential anti-HIV-1, anticancer, and antimicrobial agents.
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.
Rida
Samia M
SM
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Alexandria, Egypt.
El-Hawash
Soad A M
SA
Fahmy
Hesham T Y
HT
Hazza
Aly A
AA
El-Meligy
Mostafa M M
MM
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001572:Benzofurans / Q000138:chemical synthesis* / Q000494:pharmacology*; D015496:CD4-Positive T-Lymphocytes / Q000821:virology; D045744:Cell Line, Tumor; D003500:Cyclization; D004353:Drug Evaluation, Preclinical; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D007202:Indicators and Reagents; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular
D019380:Anti-HIV Agents; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D001572:Benzofurans; D007202:Indicators and Reagents