Synthesis, in-Vitro Cytotoxicity and Antimicrobial Evaluations of Some Novel Thiazole Based Heterocycles

Abstract

Condensation of rhodanine (1) with pyrazol-3(2H)-one derivatives (2a–f) gave 5-substituted-2-thioxo-1,3-thiazolidin-4-one derivatives (3a–f). Reaction of compound (1) with 2-arylmethylidene-malononitrile (4a–d) yielded the unexpected derivatives (5a–d). The latter compounds were subjected to cyclization reactions with malononitrile under different basic conditions, hydroxylamine hydrochloride and/or thiourea to furnish the fused thiazole derivatives (6a–d) and (8–10a–d). Coupling of (1) with diazotized aromatic amines (11a–c) in pyridine afforded the arylhydrazones (12a–c). Fusion of latter compounds with malononitrile afforded the thiazolopyridazine derivatives (13a–c). The structures of the newly synthesized compounds were elucidated via spectral data and elemental analyses. The in-vitro cytotoxic activity of compounds (3a–f) against the cell line MCF-7 was evaluated. Also, the synthesized products were investigated for their antibacterial and antifungal activities against six standard organisms including the G⁺ bacteria, Staphylococcus aureus and Bacillus subtilis, G⁻ bacteria, Escherichia coli and Proteus vulgaris in addition to fungi, Candida albicans and Aspergillus flavus.

Graphical Abstract