Title:
METHOD FOR SYNTHESIS OF CHOLEST-3β,5α,6β,19-TETRAHYDROXY-24-ONE AND ITS DERIVATIVES
Document Type and Number:
WIPO Patent Application WO/2007/076655
Kind Code:
A1
Abstract:
A synthesis process of cholest-3β,5α,6β,19-tetrahydroxy-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 cholenic 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; reaction
with diacetoxy iodobenzene to give 3β-acetoxy-cholest-5α-bromo-6β,19-epoxy-24-one; reduction
with Zn powder/glacial acetic acid system to give 3β,19-diacetoxy-cholest-5-en-24-one; oxidation
of the double bond at position 5 and 6; then hydrolysis to produce cholest-3β,5α,6β,19-tetrahydroxy-24-one; finally
reaction with methyltriphenylphosphonium bromide to produce 24-methylene-cholest-3β,5α,6β,19-tetraol; and
reaction with hydrazine to give cholest-3β,5α,6β,19-tetrahydroxy-24-dihydrazone. 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. The target compounds 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/CN2006/001627
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:
| CN1448400A | 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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