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 determine the region that the molecule is biologically active. Biological activities of mentioned molecules were investigated with molecular docking analyses. The appropriate target protein (PDB codes: 1M17 for the HeLa cells and 1JQH for the C6 cells) was used for 5c and 5e molecules exhibiting the highest biological activity against HeLa and C6 cells in the docking studies. As result, it was determined that these molecules are the best candidates for the anticancer drug.© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
February 28, 2020
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