Bioorganic & Medicinal Chemistry, ( ISI ), Volume (17), No (4), Year (2009-2) , Pages (1614-1622)

Title : ( Design, synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygensae inhibitors )

Authors: Seyed Mohammad Seyedi , Hossein Eshghi , zeinab jafari , Neda Attaran Kakhki , Hamid Sadeghian , Mohammad Reza Saberi , mahdi riazi ,

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A group of 4-allyloxyaniline amides 5a–o were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compound 5e showed the best IC50 in SLO inhibition (IC50 = 0.67 ± 0.06 μM). All compounds were docked in SLO active site retrieved from RCSB Protein Data Bank (PDB entry: 1IK3) and showed that allyloxy group of compounds is oriented towards the Fe3+-OH moiety in the active site of enzyme and fixed by hydrogen bonding with two conserved His513 and Gln716. It is resulted that molecular volume of the amide moiety would be a major factor in inhibitory potency variation of the synthetic amides, where the hydrogen bonding of the amide group could also involve in the activity of the inhibitors.

Keywords

Eugenol; Esteragol; SLO; Docking; Linoleic
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@article{paperid:1019670,
author = {Seyedi, Seyed Mohammad and Eshghi, Hossein and Jafari, Zeinab and Attaran Kakhki, Neda and Sadeghian, Hamid and Mohammad Reza Saberi and Riazi, Mahdi},
title = {Design, synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygensae inhibitors},
journal = {Bioorganic & Medicinal Chemistry},
year = {2009},
volume = {17},
number = {4},
month = {February},
issn = {0968-0896},
pages = {1614--1622},
numpages = {8},
keywords = {Eugenol; Esteragol; SLO; Docking; Linoleic acid},
}

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%0 Journal Article
%T Design, synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygensae inhibitors
%A Seyedi, Seyed Mohammad
%A Eshghi, Hossein
%A Jafari, Zeinab
%A Attaran Kakhki, Neda
%A Sadeghian, Hamid
%A Mohammad Reza Saberi
%A Riazi, Mahdi
%J Bioorganic & Medicinal Chemistry
%@ 0968-0896
%D 2009

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