(1R,3aS,3bR,10aR,10bS,12aS)-1-Ethynyl-10a,12a-dimethyl-1,2,3,3a,3b,4,5,8,10,10a,10b,11,12,12a-tetradecahydro-7,8-diaza-dicyclopenta[a,h]phenanthren-1-ol | 100088-84-4

• 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: (1R,3aS,3bR,10aR,10bS,12aS)-1-Ethynyl-10a,12a-dimethyl-1,2,3,3a,3b,4,5,8,10,10a,10b,11,12,12a-tetradecahydro-7,8-diaza-dicyclopenta[a,h]phenanthren-1-ol
• 英文别名: Cyclopenta(7,8)phenanthro(2,3-C)pyrazol-1-ol, 1-ethynyl-1,2,3,3a,3b,4,5,8,10,10a,10b,11,12,12a-tetradecahydro-10a,12a-dimethyl-；(1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol
• CAS: 100088-84-4
• 化学式: C₂₂H₂₈N₂O
• 分子量: 336.477
• InChiKey: OCUCUBCZNQZRNK-LHZXLZLDSA-N

物化性质

• 沸点：
  511.7±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  48.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,3aS,3bR,10aR,10bS,12aS)-1-Ethynyl-10a,12a-dimethyl-1,2,3,3a,3b,4,5,8,10,10a,10b,11,12,12a-tetradecahydro-7,8-diaza-dicyclopenta[a,h]phenanthren-1-ol 、 甲基磺酰氯 在 吡啶 作用下， 反应 1.0h， 以31%的产率得到(1R,3aS,3bR,10aR,10bS,12aS)-1-Ethynyl-8-methanesulfonyl-10a,12a-dimethyl-1,2,3,3a,3b,4,5,8,10,10a,10b,11,12,12a-tetradecahydro-7,8-diaza-dicyclopenta[a,h]phenanthren-1-ol
  参考文献：
  名称：

  Antiandrogenic steroidal sulfonylpyrazoles

  摘要：

  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.

  DOI：

  10.1021/jm00170a008