SYNTHESIS AND ANDROGEN RECEPTOR AFFINITY OF STEROIDAL METHYLSULFONYLFURANS AND A METHYLSULFONYLTHIOPHENE

被引：16

作者：

KUMAR, V ^{[1
]}

DAUM, SJ ^{[1
]}

BELL, MR ^{[1
]}

ALEXANDER, MA ^{[1
]}

CHRISTIANSEN, RG ^{[1
]}

ACKERMAN, JH ^{[1
]}

KROLSKI, ME ^{[1
]}

PILLING, GM ^{[1
]}

HERRMANN, JL ^{[1
]}

WINNEKER, RC ^{[1
]}

WAGNER, MM ^{[1
]}

机构：

[1] STERLING WINTHROP RES INST,RES GRP,DEPT PHARMACOL,RENSSELAER,NY 12144

来源：

TETRAHEDRON | 1991年 / 47卷 / 28期

关键词：

D O I：

10.1016/S0040-4020(01)87122-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Syntheses of the unsubstituted steroidal [3,2-b]furan (3a), thiophene (3b) and [2,3-b]furan (24) are described. Lithiation of the THP ethers 18a and 18b followed by the reaction with methyl disulfide and deprotection gave the 5'-methylsulfide derivatives 19a and 19b. Oxidation of the sulfides and ethynylation provided the compounds 2a and 2b. Swern oxidation of the [2,3-b]furan 24 with DMSO/TFAA/diisopropylethylamine resulted in oxidation to the 17-ketone and introduction of a 5'-methylthio group to give 25. Ethynylation at C-17 followed by oxidation of the sulfide group provided the product 27. 5'-Methylsulfonyl[3,2-b]furanosteroid 2a bound to the rat ventral prostate androgen receptor. However, the corresponding thiophene 2b and the [2,3-b]furan 27 lacked affinity for the receptor.

引用

页码：5099 / 5110

页数：12

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