Journal of the Iranian Chemical Society, ( ISI ), Volume (12), No (9), Year (2015-9) , Pages (1501-1508)

Title : ( Dipyrimido[4,5‑b:5,4‑e][1,4]thiazine: synthesis and their enzyme inhibitory activity assessment on soybean 15‑lipoxygenase )

Authors: azam karimian , Hossein Eshghi , Mehdi Bakavoli , Ali Shiri , mohammad saadatmandzadeh , tayebe asghari shirghan , hassanali moradi ,

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A series of new derivatives of dipyrimido[4,5-b:5,4-e][1,4] thiazine were synthesized by treatment of 5-amino-6-methyl-2-morpholino-4-pyrimidinethiol (1) with 5-bromo-2,4-dichloro-6-methylpyrimidine (2) in the presence of triethylamine and ethanol and subsequently with various secondary amines in EtOH/DMF. The thioether derivative 3 and heterocyclization products 4a–f were characterized by elemental analysis and spectroscopic techniques. The 15-LO inhibitory activities of the new synthesized compounds were also evaluated. The results show that compound 4e has the best IC50 of 15-LO inhibition (IC50 = 14.4 μM) but when all the products were theoretically docked into 15-LO, the GOLD scores of compounds 4e and 4d are 43.67 and 43.39 respectively, which show the best results. We suggest that the hydrogen bond interaction between Ser489 of 15-LO and the nitrogen of piperazine ring of compound 4e appears to play major role in lipoxygenase inhibition.

Keywords

, Dipyrimidothiazines , Bioactive heterocycles, Docking, 15-Lipoxygenase, Inhibitory
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@article{paperid:1046925,
author = {Karimian, Azam and Eshghi, Hossein and Bakavoli, Mehdi and Shiri, Ali and Saadatmandzadeh, Mohammad and Asghari Shirghan, Tayebe and Moradi, Hassanali},
title = {Dipyrimido[4,5‑b:5,4‑e][1,4]thiazine: synthesis and their enzyme inhibitory activity assessment on soybean 15‑lipoxygenase},
journal = {Journal of the Iranian Chemical Society},
year = {2015},
volume = {12},
number = {9},
month = {September},
issn = {1735-207X},
pages = {1501--1508},
numpages = {7},
keywords = {Dipyrimidothiazines ، Bioactive heterocycles، Docking، 15-Lipoxygenase، Inhibitory effect},
}

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%0 Journal Article
%T Dipyrimido[4,5‑b:5,4‑e][1,4]thiazine: synthesis and their enzyme inhibitory activity assessment on soybean 15‑lipoxygenase
%A Karimian, Azam
%A Eshghi, Hossein
%A Bakavoli, Mehdi
%A Shiri, Ali
%A Saadatmandzadeh, Mohammad
%A Asghari Shirghan, Tayebe
%A Moradi, Hassanali
%J Journal of the Iranian Chemical Society
%@ 1735-207X
%D 2015

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