(1S,2S,10S,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-methylsulfonyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-ol | 127881-88-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (1S,2S,10S,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-methylsulfonyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-ol
• CAS: 127881-88-3
• 化学式: C₂₃H₃₂N₂O₃S
• 分子量: 416.585
• InChiKey: JXDALJGLXREYEZ-ZGIWMXSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1S,2S,10S,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-ol 生成 (1S,2S,10S,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-methylsulfonyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5-dien-17-ol
  参考文献：
  名称：

  CHRISTIANSEN, ROBERT G.;BELL, MALCOLM R.;DAMBRA, THOMAS E.;MALLAMO, JOHN +, J. MED. CHEM., 33,(1990) N, C. 2094-2100

  摘要：

  DOI：

文献信息

• Antiandrogenic steroidal sulfonylpyrazoles
  作者：Robert G. Christiansen、Malcolm R. Bell、Thomas E. D'Ambra、John P. Mallamo、John L. Herrmann、James H. Ackerman、Chester J. Opalka、Rudolph K. Kullnig、Richard C. Winneker

  DOI：10.1021/jm00170a008

  日期：1990.8

  The steroidal sulfonylpyrazole 1 bound to the rat ventral prostate androgen receptor in vitro; it inhibited testosterone propionate induced increases in ventral prostate weight in vivo in the castrated, immature male rat with an ED50 of 15 mg/kg po. Compound 1 lacked androgenic activity in vivo in contrast to the parent steroidal pyrazole 5, which was both androgenic and antiandrogenic. The 2'- and 5'-methylsulfonyl isomers 6 and 6a did not bind to the androgen receptor. Introduction of an alkylsulfonyl at the N-1'-position has served, therefore, to isolate the intrinsic antiandrogenic properties of the steroidal heterocycle free of apparent hormone agonist properties. Structure-activity relationship studies revealed that a methylsulfonyl group at N-1' together with a C-17 alpha-substituent were the optimal combination for in vitro androgen receptor binding, in vivo antiandrogenic potency, and a lack of androgenic activity.