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Synthesis and Crystal Structure Analysis of Histone Deacetylase Inhibitor Chidamide

Authors :
Bo Han
Xin-Yan Peng
Yan-Qing Gong
Jia-Liang Zhong
Qing-Wei Zhang
Source :
Pharmaceutical Fronts, Vol 05, Iss 02, Pp e91-e100 (2023)
Publication Year :
2023
Publisher :
Georg Thieme Verlag KG, 2023.

Abstract

Abstract Chidamide is the first oral subtype-selective histone deacetylase inhibitor approved in China for the treatment of relapsed and refractory peripheral T cell lymphoma. Due to the existence of isomers, many articles or patents have mistaken its structure. Herein we explored the synthesis of the key intermediate (E)-4-((3-(pyridin-3-yl)acrylamido)methyl)benzoic acid (A-3) and chidamide, using the condensing agent HBTU, instead of the unstable N,N'-carbonyldiimidazole. The single crystal of chidamide was determined by X-ray diffraction study. The optimized preparation process was easy to operate, and the purity of the final product can be up to 99.76%. Moreover, the structure of chidamide was established to be (E)-N-(2-amino-4-fluorophenyl)-4-((3-(pyridin-3-yl)acrylamido)methyl)benzamide.

Details

Language :
English
ISSN :
26285088 and 26285096
Volume :
05
Issue :
02
Database :
Directory of Open Access Journals
Journal :
Pharmaceutical Fronts
Publication Type :
Academic Journal
Accession number :
edsdoj.001b6e7290714639b6777d16d6caf6f0
Document Type :
article
Full Text :
https://doi.org/10.1055/s-0043-1768613