2-(2'-(N,N-dimethylaminoethyl)imino)methyl-17-(1'-methyl)estra-1,3,5(10)-triene-3-ol | 1343481-83-3

• 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-(2'-(N,N-dimethylaminoethyl)imino)methyl-17-(1'-methyl)estra-1,3,5(10)-triene-3-ol
• 英文别名: (8S,9S,13R,14S,17S)-2-[2-(dimethylamino)ethyliminomethyl]-13,17-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
• CAS: 1343481-83-3
• 化学式: C₂₄H₃₆N₂O
• 分子量: 368.563
• InChiKey: JUWLZBBPXWFPTD-DADVRMSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2'-(N,N-dimethylaminoethyl)imino)methyl-17-(1'-methyl)estra-1,3,5(10)-triene-3-ol 在 sodium tetrahydroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以0.43 g的产率得到(8S,9S,13R,14S,17S)-2-[[2-(dimethylamino)ethylamino]methyl]-13,17-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-ol
  参考文献：
  名称：

  Panchapakesan, Ganapathy; Sureshbabu, Radhakrishnan; Nachiappan, Dhatchana Moorthy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 1, p. 109 - 121

  摘要：

  DOI：
• 作为产物：
  描述：

  17β-methylestra-1,3,5(10)-trien-3-ol 在 溴乙烷 、 magnesium 、 sodium sulfate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.58h， 生成 2-(2'-(N,N-dimethylaminoethyl)imino)methyl-17-(1'-methyl)estra-1,3,5(10)-triene-3-ol
  参考文献：
  名称：

  Synthesis of 2-substituted 17β-hydroxy/17-methylene estratrienes and their in vitro cytotoxicity in human cancer cell cultures

  摘要：

  Synthesis of various types of 2-(alkylaminomethyl) and 2-(aroyl) 17 beta-estradiol analogs are reported. The synthesis of similar types of 2-substituted 17-methylene estratriene analogs was also achieved. Synthesis of chalcone derivatives of 17 beta-estradiol and 17-methylene estratriene were also realized. All these 2-substituted estratrienes were tested for their antiproliferative activity by using four different cell lines from colon, lung, glioma and breast cancers. Among the various 2-substituted estratrienes, the compounds 10d, 14a-h and 17e were found to have in vitro antiproliferative activity comparable to that of parent analogs 1-4. Comparison of the SAR pattern of these 2-susbtituted estratriene derivatives confirmed that relatively, 17-methylene estratrienes are more active than that of 17 beta-estradiol analogs. (C) 2011 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2011.08.004