Synthesis, Spectral Characterization and Pharmacological Evaluation of Novel Thiazole-Oxoindole Hybrid Compounds as Potential Anticancer Agents

Abstract

In the present study, a series of thiazole derivatives bearing 5-morpholinosulfonylindole were designed and synthesized through condensation of 5-(morpholinosulfonyl)isatin (1) with some thiazolidinone derivatives as carbon nucleophiles to afford the corresponding arylidene derivatives (2-5, 7, 8). Furthermore, many thiazole derivatives (11-15) were obtained through the reaction of thiosemicarbazone derivative (10) with many reagents such as dimethyl acetelenedicarboxylate, phencylbromide derivatives, chloroacetonitrile, chloroacetylchloride as well as chloroacetanilide. The newly synthesized compounds were characterized based on spectral (FT-IR, 1 H NMR, 13 C NMR, MS) analysis. Cytotoxicity effects of all synthesized products were tested against three cancer cell lines, MCF-7, HepG-2, HCT-116 and they showed moderate to good cytotoxic activity against the three tested cell lines. The study showed that compounds (2a, 12b and 12c) were less or almost equipotent as doxorubicin against the three cell lines HepG-2, HCT-116.

In Vitro Antimicrobial Evaluation, Single-Point Resistance Study, and Radiosterilization of Novel Pyrazole Incorporating Thiazol-4-one/Thiophene Derivatives as Dual DNA Gyrase and DHFR Inhibitors against MDR Pathogens

“…The condensation reaction proceeds through the endocyclic methylene rather than the exocyclic one. 40 The structures of 3a−d were confirmed with the help of analytical and spectroscopic data. Thus, the IR spectrum of pyrazole derivative 3b showed significant stretching absorption bands at υ 3199, 2202, and 1718 cm −1 owing to NH, cyano (CN), and carbonyl (CO) groups, respectively.…”

“…First, 2-(4-oxothiazolidin-2-ylidene) derivatives ( 1a and 1b ) were used as precursor builders to synthesize many biologically and pharmaceutically active heterocycles. , The thiazolidin-4-one derivatives 1a and 1b were coupled with 1,3-diaryl-1 H -pyrazole-4-carboxaldehyde derivatives 2a and 2b in the presence of ethanol catalyzed with piperidine to produce 4-oxo-5-((substituted-1 H -pyrazol-4-yl)­methylene)­thiazolidin-2-ylidene derivatives ( 3a , and 3b – d ) and failed to obtain 2-(4-oxo-4,5-dihydrothiazol-2-yl)-3-(1-,3-(diaryl)-1 H -pyrazol-4-yl)­acryl derivatives 4a – d . The condensation reaction proceeds through the endocyclic methylene rather than the exocyclic one . The structures of 3a – d were confirmed with the help of analytical and spectroscopic data.…”

Design, synthesis, molecular modeling, and antimicrobial potential of novel 3‐[(1H‐pyrazol‐3‐yl)imino]indolin‐2‐one derivatives as DNA gyrase inhibitors

“…The chlorosulfonyl derivative reacted with piperidine or 4-methyl piperazine 3 to afford indol-2,3-dione derivatives 3a,b according to the previously reported procedure. [28,72,73] Also, 4-arylazo-3-aminopyrazoles 7a-f were prepared using the starting…”

“…prepared according to reported methods. [28,72,73] Furthermore, pyrazol-1-yl}(phenyl)methanone (7f) were prepared according to reported methods. [85][86][87][88] The InChI codes of the investigated compounds and figures of the FMO analysis, MEP, and docking simulation are provided as the Supporting Information.…”