CONVENIENT SYNTHESIS OF 18-HYDROXYLATED CORTISOL AND PREDNISOLONE

被引：11

作者：

KUROSAWA, T

IKEGAWA, S

CHIBA, H

ITO, Y

NAKAGAWA, S

KOBAYASHI, K

TOHMA, M

机构：

[1] HIGASHI NIPPON GAKUEN UNIV,FAC PHARMACEUT SCI,ISHIKARI,HOKKAIDO 06102,JAPAN

[2] HOKKAIDO UNIV,SCH MED,DEPT LAB MED,SAPPORO,HOKKAIDO 060,JAPAN

[3] HOKKAIDO UNIV,SCH MED,DEPT CENT MICROBIOL,SAPPORO,HOKKAIDO 060,JAPAN

来源：

STEROIDS | 1992年 / 57卷 / 09期

关键词：

18,20-EPOXY-11-BETA,17-ALPHA,20-BETA,21-TETRAHYDROXYPREGN-4-EN-3-ONE; 18,20-EPOXY-11-BETA,17-ALPHA,20-BETA,21-TETRAHYDROXYPREGNA-1,4-DIEN-3-ONE; HYPOIODITE REACTION; PRIMARY ALDOSTERONISM; STEROIDS;

D O I：

10.1016/0039-128X(92)90095-Q

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

18,20-Epoxy-11-beta,17-alpha,20-beta,21-tetrahydroxypregn-4-en-3-one was synthesized by the application of hypoiodite reaction to the cortisol acetonide. The intermediary 18-iodo derivative was converted to the 11-oxo steroid by chromic acid prior to silver ion-assisted solvolysis. Removal of the protective group with hydrochloric acid was finally carried out to give the desired 11-beta,17-alpha,18,21-tetrahydroxypregn-4-ene-3,20-dione as the hemiacetal form. 18,20-Epoxy-11-beta-17-alpha,20-beta,21-tetrahydroxypregna-1,4-dien-3-one was also prepared from prednisolone through a similar reaction sequence.

引用

收藏

页码：426 / 429

页数：4

相关论文

共 13 条

[1] IMPROVED SYNTHESES OF ALDOSTERONE [J].

BARTON, DHR ;

BASU, NK ;

DAY, MJ ;

HESSE, RH ;

PECHET, MM ;

STARRATT, AN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (22) :2243-2251

[2] SYNTHESIS OF 11-DEOXY-18-HYDROXYCORTICOSTERONE AND 18-HYDROXYCORTICOSTERONE 21-ACETATES [J].

BARTON, DHR ;

DAY, MJ ;

HESSE, RH ;

PECHET, MM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (22) :2252-2256

[3] RELATIONSHIP BETWEEN INTRAMOLECULAR HYDROGEN ABSTRACTION BY ALKOXYL RADICALS AND DESHIELDING BY CORRESPONDING HYDROXY-GROUPS AS INDICATED BY NUCLEAR MAGNETIC-RESONANCE [J].

BOAR, RB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (13) :1275-1277

[4]

CHU MD, 1982, J BIOL CHEM, V257, P2218

[5]

CORRIE JET, 1985, CLIN CHEM, V31, P849

[6] 18-SUBSTITUTED STEROIDS - SYNTHESIS OF 18-HYDROXYCORTISOL (11-BETA, 17-ALPHA, 18,21-TETRAHYDROXY-4-PREGNENE-3,20-DIONE) AND 18-HYDROXYCORTISONE (17-ALPHA,18,21-TRIHYDROXY-4-PREGNENE-3,11,20-TRIONE) [J].

GOMEZSANCHEZ, CE ;

KIRK, DN ;

FARRANT, RD ;

MILEWICH, L .

JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1985, 22 (01) :141-146

[7] RECEPTOR-BINDING AND BIOLOGICAL-ACTIVITY OF 18-HYDROXYCORTISOL [J].

GOMEZSANCHEZ, EP ;

GOMEZSANCHEZ, CE ;

SMITH, JS ;

FERRIS, MW ;

FOECKING, M .

ENDOCRINOLOGY, 1984, 115 (02) :462-466

[8] REAKTIONEN VON STEROID-HYPOJODITEN .5. EINWIRKUNG VON BLEI(IV)-ACETAT-JOD AUF 11BETA-HYDROXYSTEROIDE [J].

KALVODA, J ;

ANNER, G ;

HEUSLER, K ;

WETTSTEIN, A .

HELVETICA CHIMICA ACTA, 1963, 46 (02) :618-&

[9] 18-SUBSTITUTED STEROIDS .8. AN IMPROVED SYNTHESIS OF 11-BETA,18,21-TRIHYDROXYPREGN-4-ENE-3,20-DIONE (18-HYDROXYCORTICOSTERONE) [J].

KIRK, DN ;

SLADE, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (03) :703-705

[10] REAKTIONEN VON STEROID-HYPOJODITEN .2. UBER DIE HERSTELLUNG 18-OXYGENIERTER PREGNANVERBINDUNGEN( - UBER STEROIDE .187. [J].

MEYSTRE, C ;

ANNER, G ;

WIELAND, P ;

WETTSTEIN, A ;

HEUSLER, K ;

KALVODA, J .

HELVETICA CHIMICA ACTA, 1962, 45 (04) :1317-+