Chemical Biology and Drug Design, ( ISI ), Volume (88), No (3), Year (2016-8) , Pages (460-469)

Title : ( 2-Prenylated m -Dimethoxybenzenes as Potent Inhibitors of 15-Lipoxygenase: Inhibitory Mechanis m and SAR studies )

Authors: Atena Jabbari alamdasht , Hamid Sadeghian , Alireza Salimi , Mina Mousavian , Seyed Mohammad Seyedi , Mehdi Bakavoli ,

Access to full-text not allowed by authors

Citation: BibTeX | EndNote


15-lipo-oxygenases are one of the iron-containing proteins capable of performing peroxidation of unsaturated fatty acids in animals and plants. The critical role of enzymes in the formation of inflammations, sensitivities, and some cancers has been demonstrated in mammals. The importance of enzymes has led to the development of mechanistic studies, product analysis, and synthesis of inhibitors. In this study, a series of allyl and prenyl dimethoxybenzenes were synthesized and their inhibitory potency against soybean 15-Lipo-oxygenase (L1; EC 1,13,11,12) was determined. Among the synthetic compounds, 2,6-dimethoxy-1-isopentenyl-4-methylbenzene, 2,6-dimethoxy-1-geranyl-4-methylbenzene, and 2,6-dimethoxy-1-farnesyl-4-methylbenzene showed the most potent inhibitory activity with IC50 values of 7.6, 5.3, and 0.52 μm, respectively. For some of the compounds, SAR studies showed acceptable relationship between inhibitory potency and enzyme–ligand interactions. Radical scavenging assessment results apart from the SAR studies indicate that electronic properties are the major factors for lipo-oxygenase inhibition potency of the mentioned compounds. Based on the theoretical studies, it was suggested that CH…O intramolecular hydrogen bond between ortho-methoxy oxygen and methine hydrogen atoms is one of the major factors in the stability of 2,6-dimethoxyallyl(or prenyl)benzenes radical via the planarity fixation between phenyl and allyl (or prenyl) pi orbitals.


, Radical scavenging, 2, 2-diphenylpicrylhydrazyl (DPPH), density functional theory (DFT), hydrogen bond, docking
برای دانلود از شناسه و رمز عبور پرتال پویا استفاده کنید.

author = {Jabbari Alamdasht, Atena and Hamid Sadeghian and Salimi, Alireza and Mina Mousavian and Seyedi, Seyed Mohammad and Bakavoli, Mehdi},
title = {2-Prenylated m -Dimethoxybenzenes as Potent Inhibitors of 15-Lipoxygenase: Inhibitory Mechanis m and SAR studies},
journal = {Chemical Biology and Drug Design},
year = {2016},
volume = {88},
number = {3},
month = {August},
issn = {1747-0277},
pages = {460--469},
numpages = {9},
keywords = {Radical scavenging; 2;2-diphenylpicrylhydrazyl (DPPH); density functional theory (DFT); hydrogen bond; docking},


%0 Journal Article
%T 2-Prenylated m -Dimethoxybenzenes as Potent Inhibitors of 15-Lipoxygenase: Inhibitory Mechanis m and SAR studies
%A Jabbari Alamdasht, Atena
%A Hamid Sadeghian
%A Salimi, Alireza
%A Mina Mousavian
%A Seyedi, Seyed Mohammad
%A Bakavoli, Mehdi
%J Chemical Biology and Drug Design
%@ 1747-0277
%D 2016