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Synthesis, Anticholinesterase, Antioxidant, and Anti‐Aflatoxigenic Activity of Novel Coumarin Carbamate Derivatives
Author(s) -
Kurt Belma Zengin,
Gazioglu Isil,
Kandas Nur Ozten,
Sonmez Fatih
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201800142
Subject(s) - coumarin , chemistry , carbamate , acetylcholinesterase , butyrylcholinesterase , moiety , antioxidant , glutathione , aché , enzyme , aflatoxin , stereochemistry , ethyl carbamate , cholinesterase , biochemistry , pharmacology , organic chemistry , biology , food science , wine
New coumarin derivatives with the carbamate moiety were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. 4‐methyl‐2‐oxo‐2H‐chromen‐7‐yl cycloheptylcarbamate ( 4 h ) showed the strongest inhibition against AChE with IC 50 values of 2.30 μM, and 2‐oxo‐2H‐chromen‐7‐yl‐(cyclohexylmethyl)carbamate ( 4 c ) and 4‐methyl‐2‐oxo‐2H‐chromen‐7‐yl‐(cyclohexylmethyl)carbamate ( 4 g ) were found to be the most potent BuChE inhibitors with IC 50 value of 0.003 μM and 0.004 μM, respectively. Moreover antioxidant, anti‐aflatoxigenic activities, protective effects against aflatoxin‐B1 (AFB1) in H4IIE−C3 cells and effects on glutathione s‐transferase of the synthesized compounds were investigated. The synthesized coumarin carbamates inhibited AFB1 in H4IIE−C3 cells. Western blot analyses confirmed that GSTα protein was induced in cells treated with coumarin carbamates and AFB1. These results showed that the synthesized coumarin carbamates possess a potent protective effect against AFB1.