(+/-)-8-(ethoxycarbonyl)-2,3-diphenyl-nortrop-2-ene | 188918-03-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (+/-)-8-(ethoxycarbonyl)-2,3-diphenyl-nortrop-2-ene
• 英文别名: Ethyl 2,3-diphenyl-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate
• CAS: 188918-03-8
• 化学式: C₂₂H₂₃NO₂
• 分子量: 333.43
• InChiKey: JEGBEPAQGSGEGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-8-(ethoxycarbonyl)-2,3-diphenyl-nortrop-2-ene 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 120.0h， 生成 (+/-)-2α,3α-diphenyltropane
  参考文献：
  名称：

  Synthesis and Transporter Binding Properties of 2,3-Diphenyltropane Stereoisomers. Comparison to 3β-Phenyltropane-2β-carboxylic Acid Esters

  摘要：

  2 beta,3 beta-Diphenyl-(5), 2 alpha,3 alpha-diphenyl-(6), and 2 alpha,3 beta-diphenyltropane (3) as well as 2,3-diphenyltrop-2-ene (4) were prepared in racemic form and assayed for inhibition of radioligand binding at the dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporters. Among all three transporters, compounds 4-6 bound the DA transporter with the highest affinity. The 2 beta,3 beta-diphenyltropane (5) bound the DA transporter with an IC50 value (28 nM) almost identical to that of 3 beta-phenyltropane-2 beta-carboxylic acid methyl ester (WIN 35,065-2) and has much greater selectivity relative to binding to the serotonin transporter. A comparison of the radioligand data from this study to radioligand data obtained on other WIN 35,065-2 analogs suggests that hydrophobicity of the C-2 substituent of some analogs of the WIN 35,065-2 class may be an important contributing factor to binding at the DA transporter.

  DOI：

  10.1021/jm960703k
• 作为产物：
  描述：

  (+/-)-8-(ethoxycarbonyl)-2α-phenyl-3β-phenylnortropan-2β-ol 在 氯化亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以87%的产率得到(+/-)-8-(ethoxycarbonyl)-2,3-diphenyl-nortrop-2-ene
  参考文献：
  名称：

  Synthesis and Transporter Binding Properties of 2,3-Diphenyltropane Stereoisomers. Comparison to 3β-Phenyltropane-2β-carboxylic Acid Esters

  摘要：

  2 beta,3 beta-Diphenyl-(5), 2 alpha,3 alpha-diphenyl-(6), and 2 alpha,3 beta-diphenyltropane (3) as well as 2,3-diphenyltrop-2-ene (4) were prepared in racemic form and assayed for inhibition of radioligand binding at the dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporters. Among all three transporters, compounds 4-6 bound the DA transporter with the highest affinity. The 2 beta,3 beta-diphenyltropane (5) bound the DA transporter with an IC50 value (28 nM) almost identical to that of 3 beta-phenyltropane-2 beta-carboxylic acid methyl ester (WIN 35,065-2) and has much greater selectivity relative to binding to the serotonin transporter. A comparison of the radioligand data from this study to radioligand data obtained on other WIN 35,065-2 analogs suggests that hydrophobicity of the C-2 substituent of some analogs of the WIN 35,065-2 class may be an important contributing factor to binding at the DA transporter.

  DOI：

  10.1021/jm960703k