A1 Refereed original research article in a scientific journal
Synthesis, characterization, crystal structures and biological screening of 4-amino quinazoline sulfonamide derivatives
Authors: A. Sunil Kumar, Jyothi Kudva, Manu Lahtinen, Anssi Peuronen, Rajitha Sadashiva, Damodara Naral
Publisher: ELSEVIER SCIENCE BV
Publication year: 2019
Journal: Journal of Molecular Structure
Journal name in source: JOURNAL OF MOLECULAR STRUCTURE
Journal acronym: J MOL STRUCT
Volume: 1190
First page : 29
Last page: 36
Number of pages: 8
ISSN: 0022-2860
eISSN: 1872-8014
DOI: https://doi.org/10.1016/j.molstruc.2019.04.050
Abstract
Three quinazolin-4-ylamino derivatives containing phenylbenzenesulfonamides (7a-7c) were synthesized by reacting (E)-N'-(2-cyanophenyl)-N,N-dimethyl formamidine (6) with different 4-amino-N(phenyl)benzenesulfonamides (4a-4c) and characterized by different techniques such as HRMS, IR, H-1 NMR and C-13 NMR spectroscopy. The structural properties were further examined by single crystal X-ray diffraction method. The X-ray data shows that compounds 7a and 7c contain two molecules and 7b contains one molecule in the asymmetric unit. Comparison of conformation of two distinct molecules, "A" and "B", in the asymmetric unit of 7a and 7c were studied with the aid of reported literature. The in vitro antiproliferative activity of the compounds was tested against two breast cancer cell lines (MDA-MB-231 and MCF7). Compound 7b observed as a highest potent candidate against MDA-MB-231with IC50 of 5.44 mu g/mL. Antimicrobial activity was also screened against bacterial and fungal strains. Compound 7a with chloro substitution was observed as the most potent candidate against the Gram-negative bacterial strains, whereas the compounds showed no significant activity against the fungal strain. (C) 2019 Published by Elsevier B.V.
Three quinazolin-4-ylamino derivatives containing phenylbenzenesulfonamides (7a-7c) were synthesized by reacting (E)-N'-(2-cyanophenyl)-N,N-dimethyl formamidine (6) with different 4-amino-N(phenyl)benzenesulfonamides (4a-4c) and characterized by different techniques such as HRMS, IR, H-1 NMR and C-13 NMR spectroscopy. The structural properties were further examined by single crystal X-ray diffraction method. The X-ray data shows that compounds 7a and 7c contain two molecules and 7b contains one molecule in the asymmetric unit. Comparison of conformation of two distinct molecules, "A" and "B", in the asymmetric unit of 7a and 7c were studied with the aid of reported literature. The in vitro antiproliferative activity of the compounds was tested against two breast cancer cell lines (MDA-MB-231 and MCF7). Compound 7b observed as a highest potent candidate against MDA-MB-231with IC50 of 5.44 mu g/mL. Antimicrobial activity was also screened against bacterial and fungal strains. Compound 7a with chloro substitution was observed as the most potent candidate against the Gram-negative bacterial strains, whereas the compounds showed no significant activity against the fungal strain. (C) 2019 Published by Elsevier B.V.
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