((8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)-methanesulfonic acid 2,2-dimethyl-propyl ester | 237390-55-5

• 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-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)-methanesulfonic acid 2,2-dimethyl-propyl ester
• 英文别名: 2,2-dimethylpropyl [(8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl]methanesulfonate
• CAS: 237390-55-5
• 化学式: C₂₄H₃₄O₄S
• 分子量: 418.598
• InChiKey: KKOVLTVJTABLCL-YOEKFXIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)-methanesulfonic acid 2,2-dimethyl-propyl ester 在 盐酸 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 、 N-氟代双苯磺酰胺 、 lithium bromide 作用下， 以 四氢呋喃 、 丁酮 、 苯 为溶剂， 反应 70.0h， 生成 Lithium; difluoro-((8R,9S,13S,14S)-13-methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)-methanesulfonate
  参考文献：
  名称：

  Synthesis of estrone-3-sulfate analogues bearing novel non-hydrolyzable sulfate mimetics

  摘要：

  Estrone sulfate analogues have been prepared in which the sulfate group has been replaced with an alpha,alpha-difluoromethylenesulfonate or alpha,alpha-difluoromethylenetetrazole group. The key step in these syntheses was the electrophilic fluorination of neopentylsulfonate ester and nitrile intermediates with N-fluorobenzenesulfonimide (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00732-7
• 作为产物：
  描述：

  新戊醇 、 estra-1,3,5-(10)-triene-17-one-3-methanesulfonyl chloride 在 三乙胺 作用下， 反应 16.0h， 生成 ((8R,9S,13S,14S)-13-Methyl-17-oxo-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)-methanesulfonic acid 2,2-dimethyl-propyl ester
  参考文献：
  名称：

  Synthesis of estrone-3-sulfate analogues bearing novel non-hydrolyzable sulfate mimetics

  摘要：

  Estrone sulfate analogues have been prepared in which the sulfate group has been replaced with an alpha,alpha-difluoromethylenesulfonate or alpha,alpha-difluoromethylenetetrazole group. The key step in these syntheses was the electrophilic fluorination of neopentylsulfonate ester and nitrile intermediates with N-fluorobenzenesulfonimide (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00732-7

文献信息

• The difluoromethylene group as a replacement for the labile oxygen in steroid sulfates: a new approach to steroid sulfatase inhibitors
  作者：Jennifer Lapierre、Vanessa Ahmed、Mei-Jin Chen、Mehdi Ispahany、J.Guy Guillemette、Scott D Taylor

  DOI：10.1016/j.bmcl.2003.09.089

  日期：2004.1

  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.