2-ethyl-3-hydroxy-17β-hydroxymethylestra-1,3,5(10)-triene | 1311311-62-2

• 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: 2-ethyl-3-hydroxy-17β-hydroxymethylestra-1,3,5(10)-triene
• 英文别名: (8S,9S,13S,14S,17S)-2-ethyl-17-(hydroxymethyl)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
• CAS: 1311311-62-2
• 化学式: C₂₁H₃₀O₂
• 分子量: 314.468
• InChiKey: UBSPJFUVLULCTA-AJBNAHFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-ethyl-3-hydroxy-17β-hydroxymethylestra-1,3,5(10)-triene 在 氨基磺酰氯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以76%的产率得到2-ethyl-3-O-sulfamoyl-17β-sulfamoyloxymethylestra-1,3,5(10)-triene
  参考文献：
  名称：

  Structure–Activity Relationships of C-17-Substituted Estratriene-3-O-sulfamates as Anticancer Agents

  摘要：

  The synthesis and antiproliferative activities of analogues of 2-substituted estradiol-3,17-O,O-bis-sulfamates (E2bisMATEs) are discussed. Modifications of the C-17 substituent confirm that an H-bond acceptor is essential for high activity; its optimal linkage to C-17 and the local environment in which it resides are defined. In the non-sulfamoylated series 17 beta-acyl substitution delivers 48b, the most potent compound identified to date. In the sulfamate series a number of permutations of linker and H-bond acceptor deliver excellent activity, with 55, 61, 65, 49a, and 49b proving especially promising. The in vivo potential of these compounds was explored in the NCI hollow fiber assay and also in a mouse Matrigel model of antiangiogenesis in which 49 and 55 show significant inhibitory activity.

  DOI：

  10.1021/jm200483x
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 31.0h， 生成 2-ethyl-3-hydroxy-17β-hydroxymethylestra-1,3,5(10)-triene
  参考文献：
  名称：

  Structure–Activity Relationships of C-17-Substituted Estratriene-3-O-sulfamates as Anticancer Agents

  摘要：

  The synthesis and antiproliferative activities of analogues of 2-substituted estradiol-3,17-O,O-bis-sulfamates (E2bisMATEs) are discussed. Modifications of the C-17 substituent confirm that an H-bond acceptor is essential for high activity; its optimal linkage to C-17 and the local environment in which it resides are defined. In the non-sulfamoylated series 17 beta-acyl substitution delivers 48b, the most potent compound identified to date. In the sulfamate series a number of permutations of linker and H-bond acceptor deliver excellent activity, with 55, 61, 65, 49a, and 49b proving especially promising. The in vivo potential of these compounds was explored in the NCI hollow fiber assay and also in a mouse Matrigel model of antiangiogenesis in which 49 and 55 show significant inhibitory activity.

  DOI：

  10.1021/jm200483x