Title:
METHOD FOR SYNTHESIS OF CHOLEST-5-EN-3β,19-DIHYDROXY-24-ONE AND ITS DERIVATIVES
Document Type and Number:
WIPO Patent Application WO/2007/076656
Kind Code:
A1
Abstract:
A synthesis process of cholest-5-en-3β,19-dihydroxy-24-one and its
derivatives includes the steps of: synthesis of 3β-acetoxy-cholest-5-en-24-acid
with hyodesoxycholic acid as the starting material; synthesis of 3β-acetoxy-cholest-5-en-24-acid
chloride by reaction with thionyl chloride; reaction with isopropylcadmium
reagent under ultrasonic irradiation to produce 3β-acetoxy-cholest-5-en-24-one;
then reaction with N-bromosuccinimide/water solution of perchloric acid system
to obtain 3β-acetoxy-cholest-5α-bromo-6β-hydroxy-24-one;
oxidative ring-closing reaction to give 3β-acetoxy-cholest-5α-bromo-6β,19-epoxy-24-one;
reduction with Zn powder/glacial acetic acid system or Zn powder/alcohol system
to give 3β,19-diacetoxy-cholest-5-en-24-one or 3β-acetoxy-cholest-5-en-19-hydroxy-24-one;
then alkaline hydrolysis to produce cholest-5-en-3β,19-dihydroxy-24-one;
finally reaction with methyltriphenylphosphonium bromide to produce 24-methylene-cholest-5-en-3β,19-diol.
The synthesis process according to the invention has the characteristic of lower
price, material availability, scientific and reasonable synthetic routes,
higher yield, and the like. Both of cholest-5-en-3β,19-dihydroxy-24-one
and 24-methylene-cholest-en-3β,19-diol have significantly protective
effect on neuronal apoptosis evoked by low K+.
Inventors:
YAN GUANGMEI (CN)
ZHANG JINGXIA (CN)
QIU PENGXIN (CN)
HUANG YIJUN (CN)
LI QUN (CN)
ZHANG JINGXIA (CN)
QIU PENGXIN (CN)
HUANG YIJUN (CN)
LI QUN (CN)
Application Number:
PCT/CN2006/001628
Publication Date:
July 12, 2007
Filing Date:
July 10, 2006
Export Citation:
Assignee:
UNIV SUN YAT SEN (CN)
YAN GUANGMEI (CN)
ZHANG JINGXIA (CN)
QIU PENGXIN (CN)
HUANG YIJUN (CN)
LI QUN (CN)
YAN GUANGMEI (CN)
ZHANG JINGXIA (CN)
QIU PENGXIN (CN)
HUANG YIJUN (CN)
LI QUN (CN)
International Classes:
C07J9/00; C07J75/00
Foreign References:
| CN1448399A | 2003-10-15 | |||
| US5637691A | 1997-06-10 |
Other References:
MORIARTY R. ET AL.: "Synthesis of squalamine. A steroidal antibiotic from the shark", TETRAHEDRON LETT., vol. 35, no. 44, 1994, pages 8103 - 8106, XP000572370
Attorney, Agent or Firm:
GUANGZHOU ZHIYOU PATENT & TRADEMARK AGENCY CO., LTD. (100 XianLieZhong Road Guangzhou, Guangdong 0, CN)
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