Synthesis, characterization, crystal structure, Hirshfeld interaction and bio-evaluation studies of 4-amino quinazoline sulfonamide derivatives
| Autor: | A. Sunil Kumar, U. Vishwanatha, Jyothi Kudva, S. Madan Kumar, Damodara Naral, Vasantha Kumar |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Chemistry Organic Chemistry Crystal structure Carbon-13 NMR Triclinic crystal system 010402 general chemistry 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry Crystallography chemistry.chemical_compound Intramolecular force Quinazoline Proton NMR Single crystal Spectroscopy Monoclinic crystal system |
| Zdroj: | Journal of Molecular Structure. 1167:142-153 |
| ISSN: | 0022-2860 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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