Premium
Synthesis, in vitro Antimicrobial, and Cytotoxic Activities of New 1,3,4‐Oxadiazin‐5( 6H )‐one Derivatives from Dehydroabietic Acid
Author(s) -
Jin XiaoYan,
Zhang KangPing,
Chen Hao,
Miao TingTing,
Wang ShiFa,
Gu Wen
Publication year - 2018
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201700358
Subject(s) - chemistry , hela , antimicrobial , in vitro , bacillus subtilis , cytotoxicity , stereochemistry , mtt assay , serial dilution , carbon 13 nmr , minimum inhibitory concentration , bacteria , organic chemistry , biochemistry , medicine , alternative medicine , pathology , biology , genetics
A series of new 1,3,4‐oxadiazin‐5( 6H )‐one derivatives ( 6a–n ) of dehydroabietic acid were designed and synthesized as potential antimicrobial and antitumor agents. Their structures were characterized by IR, 1 H NMR, 13 C NMR, MS, and elemental analyses. All the title compounds were evaluated for their antimicrobial activity against four bacterial and three fungal strains using the serial dilution method. Among them, compound 6e showed the highest antibacterial activity against Bacillus subtilis with a minimum inhibitory concentration (MIC) value of 1.9 μg/mL. In addition, the in vitro cytotoxic activities of the title compounds were also assayed against three human carcinoma cell lines (MCF‐7, SMMC‐7721, and HeLa) through the MTT colorimetric method. As a result, compounds 6b , 6g , 6k, and 6m exhibited significant inhibition against at least one cell line with IC 50 values below 10 μM. Compound 6m was especially found to be the most potent derivative with IC 50 values of 2.26 ± 0.23, 0.97 ± 0.11, and 1.89 ± 0.31 μM against MCF‐7, SMMC‐7721, and HeLa cells, respectively, comparable to positive control etoposide.