(8R,9S,13S,14S)-13-Methyl-3-(1H-tetrazol-5-ylmethyl)-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

• 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: (8R,9S,13S,14S)-13-Methyl-3-(1H-tetrazol-5-ylmethyl)-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one
• 英文别名: (8R,9S,13S,14S)-13-methyl-3-(2H-tetrazol-5-ylmethyl)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-one
• 化学式: C₂₀H₂₄N₄O
• 分子量: 336.437
• InChiKey: AUWCMZFWBXHQIK-WWNBULGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  71.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (8R,9S,13S,14S)-3-Chloromethyl-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one 在 N-甲基吡咯烷酮 、 sodium azide 、 三乙胺盐酸盐 作用下， 以 水 、 丙酮 为溶剂， 反应 4.0h， 生成 (8R,9S,13S,14S)-13-Methyl-3-(1H-tetrazol-5-ylmethyl)-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one
  参考文献：
  名称：

  The difluoromethylene group as a replacement for the labile oxygen in steroid sulfates: a new approach to steroid sulfatase inhibitors

  摘要：

  Several estrone sulfate and estradiol sulfate analogues, in which the sulfate group was replaced with an alpha, alpha-difluoromethylenesulfonate group or an alpha, alpha-difluoromethylenetetrazole group, were examined as inhibitors of steroid sulfatase (STS). These compounds were 4.5-10.5 times more potent than their non-fluorinated analogues. Moreover, the presence of the fluorines changed the mode of inhibition from mixed to competitive. The inhibitor bearing the alpha, alpha-difluoromethylenetetrazole group exhibited an affinity for STS approaching that of the natural STS substrate, estrone sulfate. Possible reasons for the enhanced affinity of the fluorinated compounds compared to their non-fluorinated counterparts are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.089