O-628

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-628
• 英文别名: methyl (1R,2S,3R,5S)-3-[bis(4-fluorophenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
• 化学式: C₂₃H₂₅F₂NO₃
• 分子量: 401.453
• InChiKey: XSYGBVSQKPLETJ-BQJUDKOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  托品酮 在 甲醇 、 sodium tetrahydroborate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 环己烷 、 苯 为溶剂， 反应 23.0h， 生成 O-628
  参考文献：
  名称：

  The Discovery of an Unusually Selective and Novel Cocaine Analog: Difluoropine. Synthesis and Inhibition of Binding at Cocaine Recognition Sites

  摘要：

  Cocaine is a stimulant drug with a high abuse liability. Although it inhibits several monamine transporters in the mammalian brain, its primary mechanism of action has been ascribed to its inhibition of the dopamine transporter. The synthesis, characterization, and receptor binding properties of all eight isomers of a unique tropane analog, 2-carbomethoxy-3-[bis(4-fluorophenyl)methoxy]tropane is described. In addition, we report that the S-enantiomer, (S)-(+)-2 beta-carbomethoxy-3 alpha-[bis(4-fluorophenyl)methoxy]tropane, Difluoropine, is a potent (IC50 10.9 nM) and selective (324 [DA/5HT]) ligand for the dopamine transporter.

  DOI：

  10.1021/jm00039a014

文献信息

• The Discovery of an Unusually Selective and Novel Cocaine Analog: Difluoropine. Synthesis and Inhibition of Binding at Cocaine Recognition Sites
  作者：Peter C. Meltzer、Anna. Y. Liang、Bertha. K. Madras

  DOI：10.1021/jm00039a014

  日期：1994.6

  Cocaine is a stimulant drug with a high abuse liability. Although it inhibits several monamine transporters in the mammalian brain, its primary mechanism of action has been ascribed to its inhibition of the dopamine transporter. The synthesis, characterization, and receptor binding properties of all eight isomers of a unique tropane analog, 2-carbomethoxy-3-[bis(4-fluorophenyl)methoxy]tropane is described. In addition, we report that the S-enantiomer, (S)-(+)-2 beta-carbomethoxy-3 alpha-[bis(4-fluorophenyl)methoxy]tropane, Difluoropine, is a potent (IC50 10.9 nM) and selective (324 [DA/5HT]) ligand for the dopamine transporter.