2β-carbomethoxy-3β-<3-(tributylstannyl)phenyl>tropane | 146725-32-8

• 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-carbomethoxy-3β-<3-(tributylstannyl)phenyl>tropane
• 英文别名: 2β-Carbomethoxy-3β-(3-tributylstannylphenyl)tropane
• CAS: 146725-32-8
• 化学式: C₂₈H₄₇NO₂Sn
• 分子量: 548.397
• InChiKey: APPDYKLYXAKXHH-AURCBSNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.48
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2β-carbomethoxy-3β-<3-(tributylstannyl)phenyl>tropane 在 碘 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到2β-carbomethoxy-3β-(3-iodophenyl)tropane
  参考文献：
  名称：

  Substituted 3-phenyltropane analogs of cocaine: synthesis, inhibition of binding at cocaine recognition sites, and positron emission tomography imaging

  摘要：

  It is now accepted that (-)-cocaine binds to specific recognition sites associated with monoamine transporters in the mammalian brain. In this study, several analogs of 3beta-phenyltropane-2beta-carboxylic acid methyl ester were prepared and their potency for inhibiting the binding of [H-3]-3beta-(4-fluorophenyl)tropane-2beta-carboxylic acid methyl ester to primate caudate-putamen was evaluated. The synthesis and binding affinity of 3beta-(3,4-dichlorophenyl)tropane-2beta-carboxylic acid methyl ester, one of the most potent cocaine congeners yet reported, is presented. The feasibility of synthesizing high-affinity ligands for cocaine recognition sites and their suitability as PET imaging ligands for cocaine receptors in vivo is demonstrated.

  DOI：

  10.1021/jm00059a010
• 作为产物：
  描述：

  六正丁基二锡 、 2β-carbomethoxy-3β-(3-bromophenyl)tropane 在 三苯基膦钯 作用下， 以 甲苯 为溶剂， 以690mg (47%)的产率得到2β-carbomethoxy-3β-<3-(tributylstannyl)phenyl>tropane
  参考文献：
  名称：

  Cocaine analogues and their use as cocaine drug therapies and

  摘要：

  揭示了对可卡因受体进行成像和治疗可卡因滥用有用的苯丙替品和CFT类似物。还揭示了对帕金森病进行成像和治疗有用的类似物。

  公开号：

  US05506359A1

文献信息

• Cocaine analogues and their use as cocaine drug therapies and
  申请人：President and Fellows of Harvard College

  公开号：US05506359A1

  公开（公告）日：1996-04-09

  Disclosed are benztropine and CFT analogs useful for imaging of cocaine receptors and treatment of cocaine abuse. Also disclosed are analogs useful for imaging and treatment of Parkinson's disease.

  揭示了对可卡因受体进行成像和治疗可卡因滥用有用的苯丙替品和CFT类似物。还揭示了对帕金森病进行成像和治疗有用的类似物。
• Substituted 3-phenyltropane analogs of cocaine: synthesis, inhibition of binding at cocaine recognition sites, and positron emission tomography imaging
  作者：P. C. Meltzer、A. Y. Liang、A. L. Brownell、D. R. Elmaleh、B. K. Madras

  DOI：10.1021/jm00059a010

  日期：1993.4

  It is now accepted that (-)-cocaine binds to specific recognition sites associated with monoamine transporters in the mammalian brain. In this study, several analogs of 3beta-phenyltropane-2beta-carboxylic acid methyl ester were prepared and their potency for inhibiting the binding of [H-3]-3beta-(4-fluorophenyl)tropane-2beta-carboxylic acid methyl ester to primate caudate-putamen was evaluated. The synthesis and binding affinity of 3beta-(3,4-dichlorophenyl)tropane-2beta-carboxylic acid methyl ester, one of the most potent cocaine congeners yet reported, is presented. The feasibility of synthesizing high-affinity ligands for cocaine recognition sites and their suitability as PET imaging ligands for cocaine receptors in vivo is demonstrated.