Design Synthesis, Molecular Docking, and in vitro Anticancer and Antibacterial Evaluation of Novel 2-(9- chloro-2,3-dimethyl-6,7-dihydro-5H-benzo [7] annulen-8-yl)-3-thiazolidin-4one

Abstract

Background: The core structure of benzo[7] annulene contains a number of natural products, and this moiety is helpful in the treatment of many pharmacological activities. The thiazolidine ring has strong antibacterial activity, multi-drug resistance in several bacterial strains, and it shows effective in pharmacological treatment.Materials and Methods: A novel series of compound were synthesized 2-(9-chloro-2,3-dimethyl-6,7-dihydro-5H-benzo[7]annulen-8- yl)-3-thiazolidin-4one (9a-i) (10a-i) and its scaffold. All the synthesized compound are purified by using ethanol for recrystallization. The protein is download from PDB 5C5S (human myosin 9b RhoGAP) and it predicted in silico studies using Autodock Vina PyRx (0.8).Results: All the derivatives are characterized by TLC and spectral analysis 1 H NMR, 13C NMR, IR, MASS. All the synthesized compounds were screened as in vitro anti-cancer, and anti-bacterial activity. Among the series of compound 9h, 9i, 10h, 10i exhibit more potent against two cancer cell lines MCF7, A549. IC50 µg/mL 9h (21.16 and 19.26µg/mL), 9i (24.21 and 20.44µg/mL), 10h (18.32 and 16.32µg/ mL), 10i (17.46 and18.28µg/mL). with the reference drugs as doxorubicin (15.29 and 12.26µg/ mL) and also screened antibacterial activity most of the compound shows promising active with reference ciprofloxacin and the molecular docking analysis results shows a good binding affinity with 5c5s protein.Conclusion: The synthesized compounds were screened in vitro evaluation of anticancer activity by using MTT assay and antibacterial evaluation of different bacterial strain by using agar diffusion method. The synthesized compound were show more active when carbon chain increases activity also increases.

Keywords: Benzo[7]annulene; Thiazolidine; MCF7; A549; Docking