[1] Wu Xiaoqing, Yu Jia, Ji Min,. Novel process for large scale synthesisof N-(4-hydroxyphenyl)retinamide [J]. Journal of Southeast University (English Edition), 2008, 24 (2): 247-249. [doi:10.3969/j.issn.1003-7985.2008.02.025]

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Novel process for large scale synthesisof N-(4-hydroxyphenyl)retinamide()

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Journal of Southeast University (English Edition)[ISSN:1003-7985/CN:32-1325/N]

Volumn:

24

Issue:

2008 2

Page:

247-249

Research Field:

Chemistry and Chemical Engineering

Publishing date:

2008-06-03

Info

Title:

Novel process for large scale synthesisof N-(4-hydroxyphenyl)retinamide

Author(s):

Wu Xiaoqing;  Yu Jia;  Ji Min

School of Chemistry and Chemical Engineering, Southeast University, Nanjing 210009, China

Keywords:

4-HPR;  large scale;  synthesis;  anticancer

PACS:

TQ016

DOI:

10.3969/j.issn.1003-7985.2008.02.025

Abstract:

A method to synthesize anticancer drug N-(4-hydroxyphenyl)retinamide(4-HPR)on a large scale is described.It consists of the preferred steps of reacting all-trans retinoic acid with thionyl chloride to form retinoyl chloride and then reacting with triethylamine to generate retinoyl ammonium salt which in turn is reacted with p-aminophenol to eventually produce 4-HPR.This process can overcome many scale-up challenges that exist in the methods reported in the literature and provide an easy, mild and high yield route for large scale synthesis of 4-HPR.Moreover, the effects of the molar ratios of the reagents on the yield are examined.The best molar ratios are a 2.0 molar equivalence of thionyl chloride and a 3.0 molar equivalence of p-aminophenol to retinoic acid, and the total yield is 80.7%.

References:

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[8] Fanjul A N, Delia D, Pierotti M A, et al.4-hydroxyphenyl retinamide is a highly selective activator of retinoid receptors [J].Journal of Biological Chemistry, 1996, 271(37):22441-22446.
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[10] Um S J, Kwon Y J, Han H S, et al.Synthesis and biological activity of novel retinamide and retinoate derivatives [J].Chemical and Pharmaceutical Bulletin, 2004, 52(5):501-506.
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Memo

Memo:

Biographies: Wu Xiaoqing(1982—), female, graduate;Ji Min(corresponding author), female, doctor, professor, jimin@seu.edu.cn.
Citation: Wu Xiaoqing, Yu Jia, Ji Min.Novel process for large scale synthesis of N-(4-hydroxyphenyl)retinamide[J].Journal of Southeast University(English Edition), 2008, 24(2):247-249.

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