Synthesis of 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene Derivatives and Evaluations of Their Carbonic Anhydrase Isoenzymes Inhibitory Effects
Özet
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 K(i)s 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.
Anahtar kelimeler
Atıf için künye
ARTUNC, T., Çetinkaya, Y., GOCER, H., Gülçin, İ., MENZEK, A., Şahin, E., & SUPURAN, C. T. (2016). Synthesis of 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene Derivatives and Evaluations of Their Carbonic Anhydrase Isoenzymes Inhibitory Effects. CHEMICAL BIOLOGY & DRUG DESIGN, 87(4), 594–607. https://doi.org/10.1111/cbdd.12695
BibTeX
@article{artunc2016-66772,
author = {ARTUNC, Tekin and Çetinkaya, Yasin and GOCER, Hulya and Gülçin, İlhami and MENZEK, Abdullah and Şahin, Ertan and SUPURAN, Claudiu T.},
title = {Synthesis of 4-[2-(3,4-dimethoxybenzyl)cyclopentyl]-1,2-dimethoxybenzene Derivatives and Evaluations of Their Carbonic Anhydrase Isoenzymes Inhibitory Effects},
journal = {CHEMICAL BIOLOGY & DRUG DESIGN},
year = {2016},
volume = {87},
number = {4},
pages = {594--607},
issn = {1747-0277},
doi = {10.1111/cbdd.12695},
url = {https://akademik.atauni.edu.tr/yayinlar/66772-synthesis-of-4-2-34-dimethoxybenzylcyclopentyl-12-dimethoxybenzene-derivatives}
}