Polycyclic Aromatic Compounds, Year (2019-7)

Title : ( Synthesis, Characterization and In Vitro Antibacterial Evaluation of Novel 4-(1-(Pyrimidin-4-yl)Ethyl)-12H-Pyrimido[4′,5′:5,6][1,4]Thiazino[2,3-b]Quinoxaline Derivatives )

Authors: Toktam Afrough , Mehdi Bakavoli , Hossein Eshghi , حمید بیضایی , محمدرضا مقدم منش ,

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Abstract

A new methodology for the synthesis of 4-(1-(pyrimidin-4-yl)ethyl)-12H-pyrimido[40,50:5,6][1,4]thiazino[2,3-b]quinoxaline derivatives 5a-g was introduced. Condensation of 5-bromo-4-[1-(5-bromo-2,6-dichloropyrimidin-4-yl)ethyl]-2-chloro-6-methylpyrimidine 2 and 3-aminoquinoxaline-2-thiol 3 gave either regioisomers 4 or 40. The computational and spectral data of both regioisomers confirmed the occurrence of the S/N type Smiles rearrangement during the course of the reaction. Treatment of the foregoing compound with various secondary amines gave several new 4-(1-(pyrimidin-4-yl)ethyl)-12H-pyrimido[40,50:5,6][1,4]-thiazino[2,3-b]quinoxaline derivatives 5a-g. The newly synthesized compounds were evaluated for their potential antibacterial activity and the results exhibit two of the derivatives are moderately valuable compounds in comparison with three reference drugs.

Keywords

, Antibacterial activity; computational study; condensation reaction; pyrimido[40, 50:5, 6][1, 4]thiazino[ 2, 3-b]quinoxaline; regioisomer; S/N type smiles rearrangement
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@article{paperid:1075717,
author = {Afrough, Toktam and Bakavoli, Mehdi and Eshghi, Hossein and حمید بیضایی and محمدرضا مقدم منش},
title = {Synthesis, Characterization and In Vitro Antibacterial Evaluation of Novel 4-(1-(Pyrimidin-4-yl)Ethyl)-12H-Pyrimido[4′,5′:5,6][1,4]Thiazino[2,3-b]Quinoxaline Derivatives},
journal = {Polycyclic Aromatic Compounds},
year = {2019},
month = {July},
issn = {1040-6638},
keywords = {Antibacterial activity; computational study; condensation reaction; pyrimido[40;50:5;6][1;4]thiazino[ 2;3-b]quinoxaline; regioisomer; S/N type smiles rearrangement},
}

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%0 Journal Article
%T Synthesis, Characterization and In Vitro Antibacterial Evaluation of Novel 4-(1-(Pyrimidin-4-yl)Ethyl)-12H-Pyrimido[4′,5′:5,6][1,4]Thiazino[2,3-b]Quinoxaline Derivatives
%A Afrough, Toktam
%A Bakavoli, Mehdi
%A Eshghi, Hossein
%A حمید بیضایی
%A محمدرضا مقدم منش
%J Polycyclic Aromatic Compounds
%@ 1040-6638
%D 2019

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