Antiproliferative evaluation of some 2-(2-Styrylcyclopent-3-enyl) benzo[d]thiazoles: DFT and molecular docking study

Chemistry & Biodiversity
Mustafa CeylanEsra Koç

Abstract

The 2-(2-styrylcyclopent-3-enyl)benzo-[ d ]thiazoles (5a-m) were synthesized from the reaction of 7-styrylbicyclo[3.2.0]hept-2-en-6-ones (3a-m) with 2-aminobenzenethiol (4) . The antiproliferative activities of 5a-m were determined against C6 (Rat Brain Tumor) and HeLa (Human cervical carcinoma cells) cell lines using BrdU cell proliferation ELISA assay. Cisplatin and 5-fluorouracil (5-FU) were used as standards. The most active compound was 5e (2-((1S,2S)-2-((E)-4-methylstyryl)cyclopent-3-en-1-yl)benzo[ d ]thiazole) against C6 cell lines with IC 50 = 5.89 µM value (Cisplatin, IC 50 = 14.46 µM and 5-FU, IC 50 = 76.74 µM). Furthermore, the most active compound was 5c (2-((1S,2S)-2-((E)-2-methoxystyryl)cyclopent-3-en-1-yl)benzo[d]thiazole)  against Hela cell lines with IC 50 = 3.98 µM value (Cisplatin, IC 50 = 37.95 µM and 5-FU, IC 50 = 46.32 µM). Additionally, computational studies of related molecules were performed by using B3LYP/6-31G+(d,p) level in the gas phase. Experimental IR and NMR data were compared with the calculated results and were found to be compatible with each other. Molecular electrostatic potential (MEP) maps of the most active 5c against HeLa and the most active 5e against C6 were investigated, aiming to det...Continue Reading

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Citations

Nov 13, 2020·Molecular Diversity·Ayushi SethiyaShikha Agarwal

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