Open AccessSynthesis of Benzoxazole Associated Benzothiazine-4-ones and their in vitro and in silico Antimicrobial, Antioxidant Activities
Author(s) -
T. Padmini,
H. M. Vagdevi,
Usha Jinendra
Publication year - 2020
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2021.22964
Subject(s) - chemistry , lipinski's rule of five , antimicrobial , docking (animal) , protein data bank (rcsb pdb) , dpph , ascorbic acid , antioxidant , stereochemistry , candida albicans , biochemistry , in silico , organic chemistry , microbiology and biotechnology , food science , medicine , nursing , biology , gene
In present study, a series of 3-[(5-methyl-1,3-benzoxazol-2-yl)amino]-2-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones (6a-n) were synthesized and elucidated by elemental, FT-IR, 1H & 13C NMR andLC-MS studies. The in vitro antibacterial screening against Gram-positive bacterial strains such as B.subtilis, S. aureus, S. epidermidis and Gram-negative bacteria such as E. coli, P. aeruginosa wascarried in comparison with tetracycline as reference standard. Antifungal activities against differentfungal strains namely R. oryzae, A. niger, A. favus, C. albicans and S. cerevisiae have been evaluatedby comparing with fluconazole as reference standard. Compounds 6b, 6c, 6e, 6j, 6m and 6n emergedas highly potent antimicrobial agents. The DPPH radical scavenging assay of the synthesized moietiesshowed good antioxidant potency comparable to standard ascorbic acid. The molecular dockingsimulation studies of all the title compounds in their active conformation analogues with target proteins(PDB ID 2XCT-antibacterial, PDB ID 1IYL-antifungal, PDB ID 2HCK- antioxidant) exhibited goodbinding interactions in top scoring poses. The pharmacokinetic properties prediction by ADMETdescriptors and Lipinski′s rule of five endorse the properties of newly synthesized compounds to adrug molecule. The results of the docking protocols were compatible with the in vitro studies whichvalidates the potency of the molecules.