3-benzyloxy-17-glutaroyloxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile | 258277-00-8

• 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-benzyloxy-17-glutaroyloxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile
• 英文别名: 1-[[(1S,2S,4aS,10aR)-1-(Cyanomethyl)-1,2,3,4,4a,9,10,10a-octahydro-2-methyl-7-(phenylmethoxy)-2-phenanthrenyl]methyl] pentanedioate；5-[[(1S,2S,4aS,10aR)-1-(cyanomethyl)-2-methyl-7-phenylmethoxy-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-yl]methoxy]-5-oxopentanoic acid
• CAS: 258277-00-8
• 化学式: C₃₀H₃₅NO₅
• 分子量: 489.612
• InChiKey: HLOVDOBVOZUFNF-KMFVSHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  96.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-17-glutaroyloxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 以50.33%的产率得到3-hydroxy-17-glutaroyloxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile
  参考文献：
  名称：

  Evaluation of biological activity of new hemiesters of 17-hydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile

  摘要：

  In uterotrophic assay newly synthesized compounds 2-5 showed a complete loss of estrogenic activity, whereas derivatives 2-4 exhibited slight, and compound 5 higher antiestrogenic effects. On the other hand, anti-aromatase assay showed that compounds 2, 3, and 4 possess inhibition potency, although lower than standard aromatase inhibitor aminoglutethimide. Cytotoxicity of compounds 2-5, estradiol and tamoxifen against several human tumor or healthy cell lines (MCF-7, MDA-MB-231, HT-29, and MRC-5) was evaluated after short-time treatment.

  DOI：

  10.1007/s00044-010-9442-y
• 作为产物：
  描述：

  戊二酸 、 3-Benzyloxy-17-hydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile 以 吡啶 为溶剂， 反应 5.0h， 以93.08%的产率得到3-benzyloxy-17-glutaroyloxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile
  参考文献：
  名称：

  Evaluation of biological activity of new hemiesters of 17-hydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile

  摘要：

  In uterotrophic assay newly synthesized compounds 2-5 showed a complete loss of estrogenic activity, whereas derivatives 2-4 exhibited slight, and compound 5 higher antiestrogenic effects. On the other hand, anti-aromatase assay showed that compounds 2, 3, and 4 possess inhibition potency, although lower than standard aromatase inhibitor aminoglutethimide. Cytotoxicity of compounds 2-5, estradiol and tamoxifen against several human tumor or healthy cell lines (MCF-7, MDA-MB-231, HT-29, and MRC-5) was evaluated after short-time treatment.

  DOI：

  10.1007/s00044-010-9442-y

文献信息

• Evaluation of biological activity of new hemiesters of 17-hydroxy-16,17-secoestra-1,3,5(10)-triene-16-nitrile
  作者：Suzana S. Jovanović-Šanta、Silvana Andrić、Nebojša Andrić、Gordana Bogdanović、Julijana A. Petrović

  DOI：10.1007/s00044-010-9442-y

  日期：2011.9

  In uterotrophic assay newly synthesized compounds 2-5 showed a complete loss of estrogenic activity, whereas derivatives 2-4 exhibited slight, and compound 5 higher antiestrogenic effects. On the other hand, anti-aromatase assay showed that compounds 2, 3, and 4 possess inhibition potency, although lower than standard aromatase inhibitor aminoglutethimide. Cytotoxicity of compounds 2-5, estradiol and tamoxifen against several human tumor or healthy cell lines (MCF-7, MDA-MB-231, HT-29, and MRC-5) was evaluated after short-time treatment.