Synthesis, characterization, crystal structure, Hirshfeld interaction and bio-evaluation studies of 4-amino quinazoline sulfonamide derivatives

Abstract

In the present work, two new potentially active quinazolin-4-yl-aminobenzenesulfonamide derivatives, N-(5-methyl-1,2-oxazol-3-yl)-4-[(quinazolin-4-yl)amino]benzene-1-sulfonamide (4a) and N-(3,4-dimethyl-1,2-oxazol-5-yl)-4-[(quinazolin-4-yl)amino]benzene-1-sulfonamide (4b), were synthesized and the structures were confirmed by different spectroscopic techniques like FT-IR, 1H NMR, 13C NMR, HRMS and elemental analysis. The crystal structures were solved by single crystal X-ray diffraction (XRD) studies. The single crystal XRD studies revealed that the compound 4a crystallized in monoclinic crystal system in P 21/n space group with Z = 4 and compound 4b crystallized in triclinic crystal system in P-1 space group with Z = 2. The XRD study has explained the intramolecular interactions of the title compounds. The thermal behaviour was determined with the aid of differential scanning calorimetry (DSC) and thermogravimetry-differential thermal analysis (TG-DTA). Further, the Hirshfeld surface analysis with finger plots and the electrostatic potential map has shown the nature of interactions and percentage contribution from each individual intermolecular contact of these title compounds. The H⋯H interactions have maximum contributions and C⋯H, O⋯H and N⋯H also have shown major contributions to the total area of the surface. In vitro antimicrobial activity studies have disclosed that the compound 4b exhibited a moderate antibacterial activity against B. Subtilis and E. Coli strains and excellent activity against the fungal strain, A. Niger. In vitro anticancer activity of the compounds 4a and 4b was also screened against MCF 7 and MDA-MB-231 breast cancer cell lines and revealed that there is no significant effect of substitution on biological activity for the synthesized compounds.