DESIGN, SYNTHESIS, DOCKING STUDY AND PHARMACOLOGICAL EVALUATION OF NOVEL -2- (5-(1H-INDOL-3-YL)- 1, 3, 4-THIADIAZOL -2 -YLIMINO) -5 -(SUBSTITUTED BENZYLIDENE) THIAZOLIDIN-4-ONE ANALOGUESAbstract
A series of novel analogues of 2-(5-(1H-indol-3-yl)-1, 3, 4-thiadiazol-2-ylimino)- 5- (substituted benzylidene)thiazolidine-4-one have been synthesized. The structures of newly synthesized compounds were confirmed by FT-IR, 1H-NMR, 13C-NMR and Mass spectroscopy. The synthesized compounds showed significant antibacterial activity against gram-positive bacteria: Staphylococcus aureus (MTCC 3160), Bacillus subtilis (MTCC 2061), gram-negative Escherichia coli (MTCC 1652), Pseudomonas aeruginosa (MTCC 741) and antifungal activity against fungal strains: Candida albicans (MTCC 183) and Aspergillus niger (MTCC 2110). Also, their anti-inflammatory activity was evaluated by using carrageenan-induced rat paw edema method. Compounds 7d and 7h with the methoxy substitution on phenyl ring were found as active derivatives of the series, exhibited 49.86% and 49.88% inhibition respectively as compared with Diclofenac sodium. In-silico molecular docking studies of the synthesized compounds was done on crystal structures of proteins of microbes Aspergillus niger, Bacillus subtilis, Candida albicans, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and cyclooxygenase-2 using GRIP batch docking method of V-life MDS 3.0 software to study their observed activity which revealed a significant correlation between the binding score and biological activity for these compounds.
P. Taya, D. K. Mehta * and R. Das
Department of Pharmaceutical Chemistry, M.M. College of Pharmacy, Maharishi Markandeshwar (Deemed to be University), Mullana, Ambala, Haryana, India.
07 June 2018
19 August 2018
31 August 2018
01 February, 2019