(17α)-4-methyl-1'-(methylsulfonyl)-1'H-pregn-4-en-20-yno<3,2-c>pyrazol-17-ol | 107000-37-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (17α)-4-methyl-1'-(methylsulfonyl)-1'H-pregn-4-en-20-yno<3,2-c>pyrazol-17-ol
• 英文别名: (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,9,18-trimethyl-6-methylsulfonyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4,7,9-trien-17-ol
• CAS: 107000-37-3
• 化学式: C₂₄H₃₂N₂O₃S
• 分子量: 428.596
• InChiKey: YGJRPZQWJUJYRN-NHXPLCAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  30.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.19
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-methyl-1'H-androst-4-eno<3,2-c>pyrazol-17-one cyclic 17-(1,2-ethanediyl acetal) 在 吡啶 、 甲基溴化镁 、 溶剂黄146 作用下， 反应 4.3h， 生成 (17α)-4-methyl-1'-(methylsulfonyl)-1'H-pregn-4-en-20-yno<3,2-c>pyrazol-17-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

文献信息

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

  DOI：——

  日期：——