(8'R,9'S,10'R,13'S,14'S,17'S)-17'-(4-hydroxybut-1-ynyl)-10',13'-dimethylspiro[1,3-dioxolane-2,3'-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-17'-ol | 288160-11-2

• 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,17'S)-17'-(4-hydroxybut-1-ynyl)-10',13'-dimethylspiro[1,3-dioxolane-2,3'-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-17'-ol
• CAS: 288160-11-2
• 化学式: C₂₅H₃₆O₄
• 分子量: 400.558
• InChiKey: IWSIILSZGHJNAQ-CKOZHMEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8'R,9'S,10'R,13'S,14'S,17'S)-17'-(4-hydroxybut-1-ynyl)-10',13'-dimethylspiro[1,3-dioxolane-2,3'-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-17'-ol 在 盐酸 、 甲醇 、 sodium azide 、 TEA 、 水 、 三乙基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (8R,9S,10R,13S,14S,17S)-17-(4-Amino-but-1-ynyl)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
  参考文献：
  名称：

  Synthesis and evaluation of geldanamycin–testosterone hybrids

  摘要：

  Geldanamycin (GDM) binds to the Hsp90 chaperone protein resulting in the degradation of several important signaling proteins. A series of GDM-testosterone linked hybrids has been synthesized and evaluated for activity against prostate cancer cell lines. The hybrid with the greatest activity exhibits potent and selective cytotoxicity against prostate cancer cells containing the androgen receptor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00208-0
• 作为产物：
  描述：

  (8'R,9'S,10'R,13'S,14'S,17'S)-17'-[4-[tert-butyl(dimethyl)silyl]oxybut-1-ynyl]-10',13'-dimethylspiro[1,3-dioxolane-2,3'-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-17'-ol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(8'R,9'S,10'R,13'S,14'S,17'S)-17'-(4-hydroxybut-1-ynyl)-10',13'-dimethylspiro[1,3-dioxolane-2,3'-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-17'-ol
  参考文献：
  名称：

  Synthesis and evaluation of geldanamycin–testosterone hybrids

  摘要：

  Geldanamycin (GDM) binds to the Hsp90 chaperone protein resulting in the degradation of several important signaling proteins. A series of GDM-testosterone linked hybrids has been synthesized and evaluated for activity against prostate cancer cell lines. The hybrid with the greatest activity exhibits potent and selective cytotoxicity against prostate cancer cells containing the androgen receptor. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00208-0