Synthesis and characterization of novel multi heteronuclear compounds bearing bis-thiazolidinone, bis-spirotriazole and bisspirothiadiazole moieties and evaluation of their biological property

Abstract

Thiazolidinone-based molecules are attractive targets in the rational design of drug-like compounds, which possess anti-inflammatory, antioxidant, antitumor, choleretic, diuretic, and other activities. On the point of these views, a series of novel heteronuclear bis-thiazolidinone derivatives 3(a-j) have been achieved by the cyclization of bis-thiosemicarbazones 2(a-j) with chloroacetic acid and sodium acetate and obtained moderate to good yield. Triazole and their derivatives have gained importance amongst different five membered heterocyclic systems as they constitute the structural features of many bioactive compounds. Triazole derivatives possess wide variety of pharmacological activities such as antimicrobial, antifungal, antiviral, antitubercular and anticancer.A convenient and facile method for the synthesis and characterization of bis-spirotriazole 4(a-j) have been developed by heating ethanolic solution of bis-thiosemicarbazones 2(a-j) in presence of catalytic amount of HCl and obtained moderate to good yield. The fascinating aromatic thiadiazole is a structurally active pharmacophore and have great interest for researchers due to its versatile and wide array of biological activities in the field of medicine, pharmacology and pharmaceutics. On the point of these views, a series of novel heteronuclear bis-spiro thiadiazolederivatives 5(a-j) have been achieved by the cyclization of bis-thiosemicarbazones (2a-j) with acetic anhydride and obtained moderate to good yield. The structures of the synthesized heterocyclic compounds were characterized by chemical and spectroscopic methods such as IR, 1H NMR and 13C NMR. Optical rotation measurement showed very minor optical activity. All the synthesized compounds have been screened for their antimicrobial activity against Gram-positive and Gram-negative bacteria such as Staphylococcus Aureus, Bacillus licheniformis, Klebsiella pneumoniae, Escherichia coli and antifungal activity against Aspergillus Niger and evaluated in vitro cytotoxic activity against human cancer cell line (HeLa cell), using MTT assays but no antimicrobial activity and no cytotoxic property was observed.