11 beta-aryl steroids in the androstene series. The role of the 11 beta-region in steroid progesterone receptor interaction

被引:20
作者
Cleve, A
Fritzemeier, KH
Heinrich, N
Klar, U
MullerFahrnow, A
Neef, G
Ottow, E
Schwede, W
机构
[1] Research Laboratories of Schering AG
关键词
D O I
10.1016/0040-4020(95)00983-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses of 11 beta-arylandrost-4-en-3-one 24 and the corresponding 9 beta,19-cyclo derivative 8 are described Steric interaction between C-19 and the aryl residue effects conformational changes of the steroid ring system that result in reduced affinity for the progesterone receptor. The conformation of 11 beta-arylandrostenes is discussed in comparison with known antiprogestational steroids.
引用
收藏
页码:1529 / 1542
页数:14
相关论文
共 14 条
[1]  
CLEVE A, UNPUB
[2]  
CLEVE A, 1990, Patent No. 404283
[3]   THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].
DEWAR, MJS ;
ZOEBISCH, EG ;
HEALY, EF ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909
[4]  
HERRMANN C, 1986, LIEBIGS ANN CHEM, P1317
[5]   INFLUENCE OF BULKY 11-BETA-SUBSTITUENTS ON REACTIVITY OF ESTRENE DERIVATIVES [J].
NEEF, G ;
SAUER, G ;
WIECHERT, R .
TETRAHEDRON LETTERS, 1983, 24 (47) :5205-5208
[6]   NEW STEROIDS BY SIMMONS-SMITH METHYLENATION AND SUBSEQUENT REARRANGEMENT [J].
NEEF, G ;
CLEVE, G ;
OTTOW, E ;
SEEGER, A ;
WIECHERT, R .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4143-4146
[7]  
NEEF G, 1988, Patent No. 3842646
[8]  
NEEF G, 1989, TRENDS MED CHEM, P581
[9]   SYNTHESIS AND BIOLOGICAL TESTING OF 4'-(DIMETHYLAMINO)-17-BETA-HYDROXY-17-ALPHA-(1-PROPYNYL)BENZO[12,12A]-11-ALPHA,18-CYCLO-12A,12B-DIHOMO-13-ALPHA-ESTR-4-EN-3-ONE - AN INTERESTING RU-38-486 ANALOG [J].
OTTOW, E ;
BEIER, S ;
ELGER, W ;
FRITZEMEIER, KH ;
NEEF, G ;
WIECHERT, R .
STEROIDS, 1994, 59 (03) :185-189
[10]  
RITTER K, 1993, SYNTHESIS-STUTTGART, P735