Synthesis of new 3-(substituted-phenyl)-N-(2-hydroxy-2-(substituted-phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives as antiproliferative agents

Abstract

In the present work, we report the synthesis of a series of 3-(substituted phenyl)-N-(2-hydroxy-2-(substituted-phenyl)ethyl)-N-methylthiophene-2-sulfonamide derivatives through Suzuki and Buchwald reaction. We have optimized methodology for targets from milligram to multi-gram scale. The newly synthesized compounds were characterized by 1H NMR, 19F NMR, 13C NMR, LC-MS techniques and purity was further checked by HPLC. The compounds were evaluated for their in-vitro antiproliferative activity against MCF-7, HeLa, A-549 and Du-145 cancer cell lines by CCK-8 assay. The preliminary bioassay suggests that most of the compounds show antiproliferation with different degrees and 5-fluorouracil was used as positive control. Among these compounds 2d, 2g, 2i, 4e, 4h and 4k are most active compared to the standard. All the synthesized compounds show IC50 values from 1.82-9.52 µM in different cell lines. Amongst these, compounds 2d, 2g, 2i, 4e, 4h and 4k were most potent, with IC50 values ranging from 1.82-4.28 µM in different cell lines.

Synthesis and Anticancer Evaluation of Benzenesulfonamide Derivatives

“…In view of the above considerations, in continuation of our previous work on triazoles, pyrimidine, thiazoles and thiazolidinones of pharmaceutical interest [24][25][26][27][28][29][30] we report here on the synthesis and anticancer activity of new 3-(indoline-1-carbonyl)-N-(substituted) benzene sulfonamide analogs.…”

SYNTHESIS OF NOVEL SUBSTITUTED-BENZO[d]THIAZOLE-2,4-DICARBOXAMIDES HAVING KINASE INHIBITION AND ANTI-PROLIFERATIVE ACTIVITY

“…9 Some derivatives comprising thiophene nuclei acts as anti-proliferative agents. [10][11][12] Neural precursor cell expressed, developmentally down-regulated 8 (NEDD8) activating small molecule-drug conjugates enzymes inhibitors, 13 Raf kinase inhibitor protein (RKIP), 14 poly-ADP-ribose polymerases (PARP) and topoisomerase (TOPO) inhibitors. 15 Some benzthiazole forms key building block of some of the biologically active derivatives.…”

Synthesis and Antimicrobial Screening of 5-(Substituted Phenyl)-N-(2-Oxo-2-(Substituted Phenyl)ethyl)-N-Methylfuran-2-Sulfonamide Derivatives

“…20 Heterocyclic nuclei when coupled with different substituents in different reaction sequesces like Buchwald, Suzuki, peptide, oxidation or reduction reactions results novel heterocycles show variety of biological activities. [21][22][23] For example, benzodifuran scaffold can be easily utilized as dyes in solar cells, 24 building blocks for optoelectronic devices 25 and transistors. 26 By considering the varied biological importance of furanes and sulfonamides and in continuation of research on heterocyclic compounds in our group for the development of antimicrobial and anticancer agent [27][28][29] we have synthesized a series of 5-(substituted phenyl)-N-(2-oxo-2-(substituted phenyl)ethyl)-N-methylfuran-2-sulfonamide derivatives (4a-4m) depicted in Scheme 1 and tested their antimicrobial activity.…”