First synthesis of 22-oxa-chenodeoxycholic acid analogue

Yaoling Wang; Qiming Yue; Yi Zhao; Shubing Qiu; Yao Peng; Jue Li; Tao Zhang; Li Hai; Li Guo; Yong Wu

doi:10.1016/j.steroids.2016.04.004

First synthesis of 22-oxa-chenodeoxycholic acid analogue

Steroids. 2016 Jun:110:70-76. doi: 10.1016/j.steroids.2016.04.004. Epub 2016 Apr 23.

Authors

Yaoling Wang¹, Qiming Yue¹, Yi Zhao¹, Shubing Qiu¹, Yao Peng¹, Jue Li¹, Tao Zhang², Li Hai¹, Li Guo³, Yong Wu⁴

Affiliations

¹ Key Laboratory of Drug Targeting and Drug Delivery Systems, West China School of Pharmacy, Sichuan University, Chengdu 610041, PR China.
² ChengDu Military General Hospital, Chengdu 610083, PR China.
³ Key Laboratory of Drug Targeting and Drug Delivery Systems, West China School of Pharmacy, Sichuan University, Chengdu 610041, PR China. Electronic address: guoli@scu.edu.cn.
⁴ Key Laboratory of Drug Targeting and Drug Delivery Systems, West China School of Pharmacy, Sichuan University, Chengdu 610041, PR China. Electronic address: wyong@scu.edu.cn.

PMID: 27091765
DOI: 10.1016/j.steroids.2016.04.004

Abstract

In this study, we report the first synthesis of 22-oxa-chenodeoxycholic acid analogue via androstenedione and progesterone, in 11 and 8 steps with overall yields of 6.4% and 12.7%, respectively. We anticipate this will help to facilitate the development of new drugs.

Keywords: Analogue; Chenodeoxycholic acid; Oxa; Synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Androstenedione / chemistry
Chenodeoxycholic Acid / analogs & derivatives*
Chenodeoxycholic Acid / chemical synthesis*
Chenodeoxycholic Acid / chemistry
Drug Design
Progesterone / chemistry

Substances

Chenodeoxycholic Acid
Androstenedione
Progesterone