STUDIES ON ANABOLIC-STEROIDS .9. TERTIARY SULFATES OF ANABOLIC 17-ALPHA-METHYL STEROIDS - SYNTHESIS AND REARRANGEMENT

被引:32
作者
BI, HG
MASSE, R
JUST, G
机构
[1] UNIV QUEBEC,INST NATL RECH SCI SANTE,245 HYMUS BLVD,POINTE CLAIRE H9R 1G6,QUEBEC,CANADA
[2] MCGILL UNIV,DEPT CHEM,MONTREAL H3A 2T5,QUEBEC,CANADA
基金
加拿大自然科学与工程研究理事会;
关键词
STEROIDS; TERTIARY SULFATES; 17-ALPHA-METHYL STEROIDS; 17-BETA-METHYL STEROIDS; 17,17-DIMETHYL-18-NORANDROST-13(14)-ENES; NMR;
D O I
10.1016/0039-128X(92)90048-E
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
A simple and convenient method has been developed to prepare sulfates of anabolic 17-beta-hydroxy-17-alpha-methyl steroids. The sulfates of methandienone, 17-alpha-methyltestosterone, mestanolone, oxandrolone, and stanozolol were prepared. Different A-ring functions were not affected under the sulfation condition. The buffered hydrolyses of these sulfates provided the 17-epimers of the original steroids and 17, 17-dimethyl-18-nor-13(14)-ene steroids, presumably via the 17-carbocations.
引用
收藏
页码:306 / 312
页数:7
相关论文
共 20 条
[1]   C-13 NMR-STUDIES .69. C-13 NMR-SPECTRA OF STEROIDS - SURVEY AND COMMENTARY [J].
BLUNT, JW ;
STOTHERS, JB .
ORGANIC MAGNETIC RESONANCE, 1977, 9 (08) :439-464
[2]  
BREITMAIER E, 1987, CARBON 13 NMR SPECTR, P107
[3]   STUDIES ON ANABOLIC-STEROIDS - THE MASS-SPECTRA OF 17-ALPHA-METHYL-17-BETA-HYDROXY-1,4-ANDROSTADIEN-3-ONE (DIANABOL) AND ITS METABOLITES [J].
DURBECK, HW ;
BUKER, I .
BIOMEDICAL MASS SPECTROMETRY, 1980, 7 (10) :437-445
[4]   STEROID CONJUGATES .4. PREPARATION OF STEROID SULFATES WITH TRIETHYLAMINE-SULFUR TRIOXIDE [J].
DUSZA, JP ;
JOSEPH, JP ;
BERNSTEIN, S .
STEROIDS, 1968, 12 (01) :49-+
[5]   DETERMINATION OF METHANDROSTENOLONE AND ITS METABOLITES IN EQUINE PLASMA AND URINE BY COUPLED-COLUMN LIQUID-CHROMATOGRAPHY WITH ULTRAVIOLET DETECTION AND CONFIRMATION BY TANDEM MASS-SPECTROMETRY [J].
EDLUND, PO ;
BOWERS, L ;
HENION, J .
JOURNAL OF CHROMATOGRAPHY-BIOMEDICAL APPLICATIONS, 1989, 487 (02) :341-356
[6]  
ENGOLFRIED O, 1963, Patent No. 1152105
[8]  
Fieser LF, 1959, STEROIDS, P467
[9]  
HADD HE, 1969, CONJUGATES STEROID H, P33
[10]   A REVIEW OF THE METHODS OF CHEMICAL SYNTHESIS OF SULFATE AND GLUCURONIDE CONJUGATES [J].
KASPERSEN, FM ;
VANBOECKEL, CAA .
XENOBIOTICA, 1987, 17 (12) :1451-1471