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Synthesis, Antimicrobial Activities, and Molecular Docking Studies of Dihydrotriazine Derivatives Bearing a Quinoline Moiety
Author(s) -
Bai Xueqian,
Chen Ying,
Liu Zhe,
Zhang Linhao,
Zhang Tianyi,
Feng Bo
Publication year - 2019
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201900056
Subject(s) - chemistry , quinoline , docking (animal) , moiety , antimicrobial , stereochemistry , gatifloxacin , antibacterial activity , pseudomonas aeruginosa , combinatorial chemistry , bacteria , biochemistry , antibiotics , organic chemistry , levofloxacin , medicine , nursing , biology , genetics
In this article, three series of dihydrotriazine derivatives bearing a quinoline moiety ( 5a , 5b , 8a – 8c , and 9a – 9m ) have been designed, synthesized, and evaluated as antibacterial agents. Compounds 8a – 8c were found to be the most potent of all of the compounds tested with an MIC value of 1 μg/mL against several Gram‐positive ( S. aureus 4220 and MRSA CCARM 3506) and Gram‐negative ( E. coli 1924) strains of bacteria. In addition, 3‐[4‐amino‐6‐(phenethylamino)‐2,5‐dihydro‐1,3,5‐triazin‐2‐yl)‐6‐[(3‐chlorobenzyl)oxy]quinolin‐2‐ol ( 8a ) showed potent inhibitory activity (MIC=2 μg/mL) against Pseudomonas aeruginosa 2742, indicating that its antibacterial spectrum is similar to those of the positive controls gatifloxacin and moxifloxacin. Structure‐activity relationships (SAR) analyses and docking studies implicated the dihydrotriazine group in increasing the antimicrobial potency of the quinoline compounds. In vitro enzyme study implied that compound 8a also displayed DHFR inhibition.