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A series of benzosuberone coupled piperazin‐1‐yl thiazolidin‐4‐one derivatives 6a‐j were synthesized from 3‐(2‐[9‐chloro‐2,3‐dimethyl‐6,7‐dihydro‐5H‐benzo[7]annulen‐8‐yl]‐4‐oxothiazolidin‐3‐yl)propanoic acid (4) and substituted piperazines/secondary amines 5a‐j using 1‐hydroxy benzotriazole, 1‐ethyl‐3‐(3‐dimethylaminopropyl)carbodiimide hydrochloride and triethyl amine in good yields and their structures were characterized by 1H NMR, 13C NMR, IR, and Mass spectra. The newly synthesized compounds were evaluated for their antimicrobial activity against bacterial strains and a fungal strain. Compounds 6f and 6g were indicated promising and broad spectrum antibacterial activity.

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In an attempt to achieve promising cytotoxic agents, a series of new (Z)‐3‐benzyl‐5‐((1‐phenyl‐3‐(3‐((1‐substituted phenyl‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)‐1H‐pyrazol‐4‐yl)methylene)thiazolidine‐2,4‐diones 10 a‐n were designed, synthesized, and characterized by 1H NMR, 13C NMR, IR, and ESI‐MS techniques. These compounds synthesized from appropriate reaction procedures with better yields. All the novel synthesized compounds 10a‐n were evaluated for their cytotoxic activity against the MCF‐7 cell line (Human breast cancer cell line) at different concentrations of 0.625, 1.25, 2.5, 5, and 10 μM, respectively. The cytotoxic evaluation assay is presented in terms of IC50 values and percentage cell viability reduction compared against standard drug cisplatin. Among all novel synthesized compounds 10a‐n, some of the representative analogues particularly 10g and 10e exhibit remarkable cytotoxic activity with IC50 values 0.454 and 0.586 μM, comparable to that of the standard drug cisplatin, and some analogues 10d, 10f, 10k, and 10m also have shown significant activity.