Design, synthesis, and in-silico study of chromen-sulfonamide congeners as potent anticancer and antimicrobial agents

A series of N-heteroaryl- 4-(1-(2-oxo-2 H -chromen-3-yl) ethylideneamino) benzenesulfonamide ( 5a- 5h) have been synthesized by the condensation reaction of appropriate N -heteroaryl- 4-amino benzenesulfonamide ( 4a-4f ) with derivatives of 3-acetyl coumarin ( 3a-3b ) in ethanol. The structures of these congeners were confirmed by 1 H/ 13 CNMR, FTIR, HRMS, elemental analysis, and their powder characteristic was measured by XRD techniques. Further, the results of antimicrobial assay for compounds 5a, 5d, and 5f proved to be potent against the terbinafine resistant Trichophyton rubrum on the basis of an acceptable MIC value of 12.5 mu g/ mL when compared to Ketoconazole. Moreover, compound 5f had shown the highest zone of inhibition against Staphylococcus aureus as compared to Gentamicin. The designed hybrid molecules were previously screened and optimized through molecular docking using AutoDock4.2 and other concomitant parameters have also been validated. The docking results of the compounds 5d, 5e, 5f , and 5h displaying binding energy in an ascending series, -9.28, -10.08, -11.88 and -12.4 Kcal/mol with the cancer causing protein further motivated for the assessment of in vitro anticancer activity. Therefore, the synthesized molecules were screened against different cancer cell lines (MDA-MB-231, MIA PaCa2, and H357cells) and the results indicated that all the compounds inhibited the cell proliferation in a concentration-dependent manner at different time points.

Automated summary

A series of N-heteroaryl-4-(1-(2-oxo-2H-chromen-3-yl)ethylideneamino)benzenesulfonamide compounds were synthesized by condensation reactions. The structures were confirmed through various analyses and their antimicrobial and anticancer activities were evaluated. The compounds exhibited good inhibitory effects against certain microorganisms and showed potential for future therapeutic applications.