Chemical Biology and Drug Design, ( ISI ), Volume (85), No (2), Year (2015-2) , Pages (216-224)

Title : ( Synthesis and Evaluation of a New Series of 3,5-bis ((5-bromo-6-methyl-2- t-aminopyrimidin-4-yl)thio)-4 H-1,2,4-triazol-4-amines and their Cyclized Products ‘Pyrimidinylthio Pyrimidotriazolothiadiazines’ as 15- Lipo-Oxygenase Inhibitors )

Authors: tayebe asghari shirghan , Mehdi Bakavoli , Mohammad Rahimizadeh , Hossein Eshghi , satar saberi , azam karimian , Farzin Hadizadeh , Moreteza Ghandadi ,

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A series of new 3,5-bis((5-bromo-6-methyl-2- t -aminopyrimidin-4 -yl)thio)-4 H-1,2,4-triazol-4-amines and their cycliz ed products ‘pyrimidinylthio pyrimidotriazolothiadiazi nes’ were designed, synthesized, and evaluated as potential inhibitors of 15-lipo-oxygenase (15-LO). Their syntheses started by initial condensation of 2:1 equivalents of pyrimidine with triazole and subsequent nucleophilic displ acement of the chlorine atoms with secon dary amines and finally cyclocondensation in the presence of NaNH . The compounds 4d and 4f showed the best IC50 2 of 15-LO inhibition (IC50= 9 and 12 l M, respectively). Compounds 4a–g were docked into 15LO. We suggest that the hydrogen bonds in quaternary nitrogen of piperazine ring of compounds 4d and 4f appea r t o play major role in lipo-oxygenase inhibition by this set of synthesized analogs and hydrophobic nature of this protein’s binding site should be considered in ongoing investigations.

Keywords

, 15-LO, 3, 5-bis((5-bro mo-6-methyl-2- t-aminopyrimidin-4-yl)thio)-4 H -1, 2, 4-triazol-4-amine, docking, heterocyclization, inhibitors, pyrimidinylthio,
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@article{paperid:1046481,
author = {Asghari Shirghan, Tayebe and Bakavoli, Mehdi and Rahimizadeh, Mohammad and Eshghi, Hossein and Saberi, Satar and Karimian, Azam and Farzin Hadizadeh and Moreteza Ghandadi},
title = {Synthesis and Evaluation of a New Series of 3,5-bis ((5-bromo-6-methyl-2- t-aminopyrimidin-4-yl)thio)-4 H-1,2,4-triazol-4-amines and their Cyclized Products ‘Pyrimidinylthio Pyrimidotriazolothiadiazines’ as 15- Lipo-Oxygenase Inhibitors},
journal = {Chemical Biology and Drug Design},
year = {2015},
volume = {85},
number = {2},
month = {February},
issn = {1747-0277},
pages = {216--224},
numpages = {8},
keywords = {15-LO; 3;5-bis((5-bro mo-6-methyl-2- t-aminopyrimidin-4-yl)thio)-4 H -1;2;4-triazol-4-amine; docking; heterocyclization; inhibitors; pyrimidinylthio; synthesis},
}

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%0 Journal Article
%T Synthesis and Evaluation of a New Series of 3,5-bis ((5-bromo-6-methyl-2- t-aminopyrimidin-4-yl)thio)-4 H-1,2,4-triazol-4-amines and their Cyclized Products ‘Pyrimidinylthio Pyrimidotriazolothiadiazines’ as 15- Lipo-Oxygenase Inhibitors
%A Asghari Shirghan, Tayebe
%A Bakavoli, Mehdi
%A Rahimizadeh, Mohammad
%A Eshghi, Hossein
%A Saberi, Satar
%A Karimian, Azam
%A Farzin Hadizadeh
%A Moreteza Ghandadi
%J Chemical Biology and Drug Design
%@ 1747-0277
%D 2015

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