(2E)-3-(3-hydroxy-17-(1'-methylene)-1,3,5(10)-estratrienyl)-1-(2',4',6'-trimethoxyphenyl)prop-2-en-1-one | 1343481-76-4

• 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: (2E)-3-(3-hydroxy-17-(1'-methylene)-1,3,5(10)-estratrienyl)-1-(2',4',6'-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-[(8S,9S,13S,14S)-3-hydroxy-13-methyl-17-methylidene-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-2-yl]-1-(2,4,6-trimethoxyphenyl)prop-2-en-1-one
• CAS: 1343481-76-4
• 化学式: C₃₁H₃₆O₅
• 分子量: 488.624
• InChiKey: RAAYBFRBRVKSFG-CNVUZBINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-hydroxy-17-methyleneestra-1,3,5(10)-trien-2-carboxaldehyde 在 盐酸 、 potassium hydroxide 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 6.0h， 生成 (2E)-3-(3-hydroxy-17-(1'-methylene)-1,3,5(10)-estratrienyl)-1-(2',4',6'-trimethoxyphenyl)prop-2-en-1-one
  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

文献信息

• Synthesis of 2-substituted 17β-hydroxy/17-methylene estratrienes and their in vitro cytotoxicity in human cancer cell cultures
  作者：Ganapathy Panchapakesan、Vasudevan Dhayalan、Nachiappan Dhatchana Moorthy、Nidhyanandan Saranya、Arasambattu K. Mohanakrishnan

  DOI：10.1016/j.steroids.2011.08.004

  日期：2011.12

  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.