A concise synthesis of pyrrole-based drug candidates from α-hydroxyketones, 3-oxobutanenitrile, and anilines

A simple and concise three-component synthesis of a key pyrrole framework was developed from the reaction between α-hydroxyketones, oxoacetonitriles, and anilines. The synthesis was used to obtain several pyrrole-based drug candidates, including COX-2 selective NSAID, antituberculosis lead candidate...

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Main Authors: Xia, Mengxin, Santoso, Mardi, Moussa, Ziad, Judeh, Zaher M. A.
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Journal Article
Language:English
Published: 2023
Subjects:
Online Access:https://hdl.handle.net/10356/169534
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author Xia, Mengxin
Santoso, Mardi
Moussa, Ziad
Judeh, Zaher M. A.
author2 School of Chemistry, Chemical Engineering and Biotechnology
author_facet School of Chemistry, Chemical Engineering and Biotechnology
Xia, Mengxin
Santoso, Mardi
Moussa, Ziad
Judeh, Zaher M. A.
author_sort Xia, Mengxin
collection NTU
description A simple and concise three-component synthesis of a key pyrrole framework was developed from the reaction between α-hydroxyketones, oxoacetonitriles, and anilines. The synthesis was used to obtain several pyrrole-based drug candidates, including COX-2 selective NSAID, antituberculosis lead candidates BM212, BM521, and BM533, as well as several analogues. This route has potential to obtain diverse libraries of these pyrrole candidates in a concise manner to develop optimum lead compounds.
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spelling ntu-10356/1695342023-07-28T15:31:49Z A concise synthesis of pyrrole-based drug candidates from α-hydroxyketones, 3-oxobutanenitrile, and anilines Xia, Mengxin Santoso, Mardi Moussa, Ziad Judeh, Zaher M. A. School of Chemistry, Chemical Engineering and Biotechnology Engineering::Chemical engineering Pyrroles Three-Component Reactions A simple and concise three-component synthesis of a key pyrrole framework was developed from the reaction between α-hydroxyketones, oxoacetonitriles, and anilines. The synthesis was used to obtain several pyrrole-based drug candidates, including COX-2 selective NSAID, antituberculosis lead candidates BM212, BM521, and BM533, as well as several analogues. This route has potential to obtain diverse libraries of these pyrrole candidates in a concise manner to develop optimum lead compounds. Nanyang Technological University Published version This research was funded by the College of Engineering (Startup Grant), Nanyang Technological University, Singapore, and by the United Arab Emirates University (UAEU), Al-Ain (Grant no.G00003918). 2023-07-24T00:50:17Z 2023-07-24T00:50:17Z 2023 Journal Article Xia, M., Santoso, M., Moussa, Z. & Judeh, Z. M. A. (2023). A concise synthesis of pyrrole-based drug candidates from α-hydroxyketones, 3-oxobutanenitrile, and anilines. Molecules, 28(3), 1265-. https://dx.doi.org/10.3390/molecules28031265 1420-3049 https://hdl.handle.net/10356/169534 10.3390/molecules28031265 36770934 2-s2.0-85147893833 3 28 1265 en NTU-SUG Molecules © 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https:// creativecommons.org/licenses/by/ 4.0/). application/pdf
spellingShingle Engineering::Chemical engineering
Pyrroles
Three-Component Reactions
Xia, Mengxin
Santoso, Mardi
Moussa, Ziad
Judeh, Zaher M. A.
A concise synthesis of pyrrole-based drug candidates from α-hydroxyketones, 3-oxobutanenitrile, and anilines
title A concise synthesis of pyrrole-based drug candidates from α-hydroxyketones, 3-oxobutanenitrile, and anilines
title_full A concise synthesis of pyrrole-based drug candidates from α-hydroxyketones, 3-oxobutanenitrile, and anilines
title_fullStr A concise synthesis of pyrrole-based drug candidates from α-hydroxyketones, 3-oxobutanenitrile, and anilines
title_full_unstemmed A concise synthesis of pyrrole-based drug candidates from α-hydroxyketones, 3-oxobutanenitrile, and anilines
title_short A concise synthesis of pyrrole-based drug candidates from α-hydroxyketones, 3-oxobutanenitrile, and anilines
title_sort concise synthesis of pyrrole based drug candidates from α hydroxyketones 3 oxobutanenitrile and anilines
topic Engineering::Chemical engineering
Pyrroles
Three-Component Reactions
url https://hdl.handle.net/10356/169534
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