[(8R,9S,13S,14S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl]-methanesulfonic acid 2,2-dimethyl-propyl ester | 669090-97-5

• 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,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl]-methanesulfonic acid 2,2-dimethyl-propyl ester
• CAS: 669090-97-5
• 化学式: C₄₀H₅₄O₄SSi
• 分子量: 659.018
• InChiKey: GGBMMFVSURIXSV-OBRFQGJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.38
• 重原子数：
  46.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.6
• 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,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-13-methyl-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 sodium hexamethyldisilazane 、 N-氟代双苯磺酰胺 作用下， 以 四氢呋喃 为溶剂， 以44%的产率得到[(8R,9S,13S,14S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl]-difluoro-methanesulfonic acid 2,2-dimethyl-propyl ester
  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
• 作为产物：
  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 咪唑 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(8R,9S,13S,14S,17S)-17-(tert-Butyl-diphenyl-silanyloxy)-13-methyl-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：

  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