2β-<(4,7-dithiaoctanoyloxy)methyl>-3β-(4-fluorophenyl)tropane | 217438-61-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 托烷生物碱
• 英文名称: 2β-<(4,7-dithiaoctanoyloxy)methyl>-3β-(4-fluorophenyl)tropane
• 英文别名: [(1R,2S,3S,5S)-3-(4-fluorophenyl)-8-methyl-8-azabicyclo[3.2.1]octan-2-yl]methyl 3-(2-methylsulfanylethylsulfanyl)propanoate
• CAS: 217438-61-4
• 化学式: C₂₁H₃₀FNO₂S₂
• 分子量: 411.605
• InChiKey: WSLCFIYYDJNWLK-ZGXWSNOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  80.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  氯乙酸酐 、 2β-<(4,7-dithiaoctanoyloxy)methyl>-3β-(4-fluorophenyl)tropane 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以39%的产率得到disopropyl 1,1-difluoro-3-aza-4-oxo-5-chloropentane-1-phosphonate
  参考文献：
  名称：

  Highly Potent Bisphosphonate Ligands for Phosphoglycerate Kinase

  摘要：

  We have synthesized a series of novel analogs of 1,3-bisphospho-D-glyceric -acid, 1,3-BPG,(3) and evaluated their binding to phosphoglycerate kinase, PGK (EC 2.7.2.3). Nonscissile methane-phosphonic acids replace the two phosphate monoesters of 1,3-BPG and lead to several stable, tight-binding mimics of this intermediate species in glycolysis. Multiple fluorine substitution for hydrogen in the alpha-methylene groups of the phosphonic acid 1,3-BPG analogs markedly improves their binding to PGK as determined by NMR analysis. The best ligands bind some 50-100 times more strongly than does the substrate 3-phospho-D-glyceric acid and show a requirement for PKa3 to be generally below 6.0, while the presence of a beta-carbonyl group seems to be of secondary importance.

  DOI：

  10.1021/jm970839y
• 作为产物：
  描述：

  甲基(1R,2S,3S,5S)-3-(4-氟苯基)-8-甲基-8-氮杂双环[3.2.1]辛烷-2-甲酸酯 在 4-二甲氨基吡啶 、 二异丁基氢化铝 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 2β-<(4,7-dithiaoctanoyloxy)methyl>-3β-(4-fluorophenyl)tropane
  参考文献：
  名称：

  TROTEC-1：一种新的高亲和力配体，用于标记多巴胺转运蛋白。

  摘要：

  DOI：

  10.1021/jm981008a

文献信息

• Highly Potent Bisphosphonate Ligands for Phosphoglycerate Kinase
  作者：David L. Jakeman、Andrew J. Ivory、Michael P. Williamson、G. Michael Blackburn

  DOI：10.1021/jm970839y

  日期：1998.11.1

  We have synthesized a series of novel analogs of 1,3-bisphospho-D-glyceric -acid, 1,3-BPG,(3) and evaluated their binding to phosphoglycerate kinase, PGK (EC 2.7.2.3). Nonscissile methane-phosphonic acids replace the two phosphate monoesters of 1,3-BPG and lead to several stable, tight-binding mimics of this intermediate species in glycolysis. Multiple fluorine substitution for hydrogen in the alpha-methylene groups of the phosphonic acid 1,3-BPG analogs markedly improves their binding to PGK as determined by NMR analysis. The best ligands bind some 50-100 times more strongly than does the substrate 3-phospho-D-glyceric acid and show a requirement for PKa3 to be generally below 6.0, while the presence of a beta-carbonyl group seems to be of secondary importance.
• TROTEC-1:  A New High-Affinity Ligand for Labeling of the Dopamine Transporter
  作者：Alexander Hoepping、Martina Reisgys、Peter Brust、Sepp Seifert、Hartmut Spies、Roger Alberto、Bernd Johannsen

  DOI：10.1021/jm981008a

  日期：1998.11.1