3-[[(1R,2S,4R,5R,8S,9S,12S)-16-hydroxy-9-methyl-6-oxo-7-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-13(18),14,16-trien-5-yl]methyl]benzamide | 1332981-46-0

• 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-[[(1R,2S,4R,5R,8S,9S,12S)-16-hydroxy-9-methyl-6-oxo-7-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-13(18),14,16-trien-5-yl]methyl]benzamide
• CAS: 1332981-46-0
• 化学式: C₂₈H₃₁NO₄
• 分子量: 445.558
• InChiKey: GENBRBKZOQFUMC-IKPVHBHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-甲酰基苯并酰胺 在 盐酸 、 20% palladium hydroxide on charcoal 、 水 、 氢气 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 23.5h， 生成 3-[[(1R,2S,4R,5R,8S,9S,12S)-16-hydroxy-9-methyl-6-oxo-7-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-13(18),14,16-trien-5-yl]methyl]benzamide
  参考文献：
  名称：

  Synthesis and preliminary evaluation of a modified estradiol-core bearing a fused γ-lactone as non-estrogenic inhibitor of 17β-hydroxysteroid dehydrogenase type 1

  摘要：

  A non-estrogenic inhibitor of 17 beta-hydroxysteroid dehydrogenase type 1 (17 beta-HSD1) was designed based on a modified 3-hydroxy-estra-1,3,5(10)-triene core having an additional five-member lactone ring and a benzamide group. The inhibitor was synthesized, fully characterized and tested for its ability to inhibit the enzyme activity. Estrogenicity was also investigated and tested on estrogen-dependent T-47D cell line. Interestingly, this steroid derivative showed inhibitory potency towards 17 beta-HSD1 and did not present residual unwanted estrogenic activity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.110