(8'R,9'S,10'R,13'S,14'S)-4',10',13'-trimethylspiro[1,3-dioxolane-2,17'-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-3'-one | 127881-93-0

• 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: (8'R,9'S,10'R,13'S,14'S)-4',10',13'-trimethylspiro[1,3-dioxolane-2,17'-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-3'-one
• CAS: 127881-93-0
• 化学式: C₂₂H₃₂O₃
• 分子量: 344.494
• InChiKey: XXRMTPQQJNBNLV-SVZPGXKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  25.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (8'R,9'S,10'R,13'S,14'S)-4',10',13'-trimethylspiro[1,3-dioxolane-2,17'-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-3'-one 在 吡啶 、 甲醇 、 sodium methylate 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 25.5h， 生成 (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]
  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
• 作为产物：
  描述：

  4-Methyl-androst-4-en-3,17-dion 生成 (8'R,9'S,10'R,13'S,14'S)-4',10',13'-trimethylspiro[1,3-dioxolane-2,17'-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-3'-one
  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：