[3-methoxyestra-1,3,5(10)-trien-17β-acetate-2-yl](3,4-dimethoxyphenyl)methanone | 1383123-19-0

• 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: [3-methoxyestra-1,3,5(10)-trien-17β-acetate-2-yl](3,4-dimethoxyphenyl)methanone
• 英文别名: [(8R,9S,13S,14S,17S)-2-(3,4-dimethoxybenzoyl)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 1383123-19-0
• 化学式: C₃₀H₃₆O₆
• 分子量: 492.612
• InChiKey: CDCLJPKFHBSXDR-ZWKDHSJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [3-methoxyestra-1,3,5(10)-trien-17β-acetate-2-yl](3,4-dimethoxyphenyl)methanone 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到[3-hydroxylestra-1,3,5(10)-trien-17β-acetate-2-yl](4-hydroxy-3-methoxyphenyl)methanone
  参考文献：
  名称：

  Gallic acid based steroidal phenstatin analogues for selective targeting of breast cancer cells through inhibiting tubulin polymerization

  摘要：

  Phenstatin analogues were synthesized on steroidal framework, for selective targeting of breast cancer cells. These analogues were evaluated for anticancer efficacy against breast cancer cell lines. Analogues 12 and 19 exhibited significant anticancer activity against MCF-7, hormone dependent breast cancer cell line. While analogues 10-14 exhibited significant anticancer activity against MDA-MB-231, hormone independent breast cancer cell line. Compound 10 showed significant oestrogen antagonistic activities with low agonistic activity in in vivo rat model. These analogues also retain tubulin polymerization inhibition activity. The most active analogue 10 was found to be non-toxic in Swiss albino mice up to 300 mg/kg dose. Gallic acid based phenstatin analogues may further be optimized as selective anti-breast cancer agents. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.03.012
• 作为产物：
  描述：

  雌二醇 3-甲基醚 17-乙酸酯 、 3,4-二甲氧基苯甲酰氯 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 [3-methoxyestra-1,3,5(10)-trien-17β-acetate-2-yl](3,4-dimethoxyphenyl)methanone
  参考文献：
  名称：

  Gallic acid based steroidal phenstatin analogues for selective targeting of breast cancer cells through inhibiting tubulin polymerization

  摘要：

  Phenstatin analogues were synthesized on steroidal framework, for selective targeting of breast cancer cells. These analogues were evaluated for anticancer efficacy against breast cancer cell lines. Analogues 12 and 19 exhibited significant anticancer activity against MCF-7, hormone dependent breast cancer cell line. While analogues 10-14 exhibited significant anticancer activity against MDA-MB-231, hormone independent breast cancer cell line. Compound 10 showed significant oestrogen antagonistic activities with low agonistic activity in in vivo rat model. These analogues also retain tubulin polymerization inhibition activity. The most active analogue 10 was found to be non-toxic in Swiss albino mice up to 300 mg/kg dose. Gallic acid based phenstatin analogues may further be optimized as selective anti-breast cancer agents. (c) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.03.012