Tekin Artunç, Yasin Çetinkaya, Hülya Göçer
Apr 1, 2016
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Influential Citations
47
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Journal
Chemical Biology & Drug Design
Abstract
Rearrangement of 1,6‐bis(3,4‐dimethoxyphenyl)hexane‐1,6‐dione (8) gave two isomeric products having cyclopentene moiety. Starting from the major product (3,4‐dimethoxyphenyl)[2‐(3,4‐dimethoxyphenyl)cyclopent‐1‐en‐1‐yl]methanone (11), eight new compounds (16–23) were obtained by the reactions such as reduction (by catalytic hydrogenation and NaBH4), nitration, 1,4‐addition, bromination, and esterification reactions. Carbonic anhydrases (CA, E.C.4.2.1.1) are ubiquitous metalloenzymes present in almost all living organism that catalyze a simple reaction, the conversion of carbon dioxide (CO2) and water (H2O) to bicarbonate ion (HCO3−) and a proton (H+). CA isoenzymes I and II (hCA I and II) inhibition effects of synthesized eleven new and four known compounds (8–13 and 15–23) were investigated. Inhibition studies of the hCA I and II with 4‐[2‐(3,4‐dimethoxybenzyl)cyclopentyl]‐1,2‐dimethoxybenzene derivatives revealed that they possess effective inhibitory potency. Cytosolic hCA I and II isoenzymes were potently inhibited by new synthesized 4‐[2‐(3,4‐dimethoxybenzyl)cyclopentyl]‐1,2‐dimethoxybenzene derivatives with Kis in the range of 313.16–1537.00 nm against hCA I and in the range of 228.31–1927.31 nm against hCA II, respectively.