4-methyl-1'-(methylsulfonyl)-1'H-androst-4-eno<3,2-c>pyrazol-17-one | 107000-38-4

• 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: 4-methyl-1'-(methylsulfonyl)-1'H-androst-4-eno<3,2-c>pyrazol-17-one
• 英文别名: (1S,2R,13R,14S,18S)-2,9,18-trimethyl-6-methylsulfonyl-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4,7,9-trien-17-one
• CAS: 107000-38-4
• 化学式: C₂₂H₃₀N₂O₃S
• 分子量: 402.558
• InChiKey: KKMSEDBNCKEHEA-NIDCRGGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  69.03
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-methyl-1'-(methylsulfonyl)-1'H-androst-4-eno<3,2-c>pyrazol-17-one 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：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  (1'S,2'R,13'R,14'S,18'S)-2',9',18'-trimethyl-6'-methylsulfonylspiro[1,3-dioxolane-2,17'-6,7-diazapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4,7,9-triene] 在 溶剂黄146 作用下， 以75%的产率得到4-methyl-1'-(methylsulfonyl)-1'H-androst-4-eno<3,2-c>pyrazol-17-one
  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