(2S,6R)-2,6-bis[2-(3-methoxyphenyl)ethyl]piperidine | 818377-31-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (2S,6R)-2,6-bis[2-(3-methoxyphenyl)ethyl]piperidine
• CAS: 818377-31-0
• 化学式: C₂₃H₃₁NO₂
• 分子量: 353.505
• InChiKey: GYERAHOQAFORJO-OYRHEFFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,6R)-2,6-bis[2-(3-methoxyphenyl)ethyl]piperidine 、 聚合甲醛 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 生成 (2S,6R)-2,6-bis[2-(3-methoxyphenyl)ethyl]-1-methylpiperidine
  参考文献：
  名称：

  Lobelane analogues as novel ligands for the vesicular monoamine transporter-2

  摘要：

  A series of lobelane analogues has been synthesized and their structure-activity relationships at the vesicular monoamine transporter-2 (VMAT2) have been evaluated. The most potent analogues in this series were the cis-2,6-piperidino analogues, 25b, 27b, 28b, and 30b, with K-i ranging from 430 to 580 nM.. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.013
• 作为产物：
  描述：

  2,6-二甲基吡啶 在 platinum(IV) oxide 氢气 、 乙酸酐 、 溶剂黄146 作用下， 20.0 ℃ 、310.26 kPa 条件下， 生成 (2S,6R)-2,6-bis[2-(3-methoxyphenyl)ethyl]piperidine
  参考文献：
  名称：

  Lobelane analogues as novel ligands for the vesicular monoamine transporter-2

  摘要：

  A series of lobelane analogues has been synthesized and their structure-activity relationships at the vesicular monoamine transporter-2 (VMAT2) have been evaluated. The most potent analogues in this series were the cis-2,6-piperidino analogues, 25b, 27b, 28b, and 30b, with K-i ranging from 430 to 580 nM.. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.013

文献信息

• Exploring the effect of N-substitution in nor-lobelane on the interaction with VMAT2: discovery of a potential clinical candidate for treatment of methamphetamine abuse
  作者：Guangrong Zheng、David B. Horton、Narsimha Reddy Penthala、Justin R. Nickell、John P. Culver、Agripina G. Deaciuc、Linda P. Dwoskin、Peter A. Crooks

  DOI：10.1039/c3md20374c

  日期：——

  A series of N-substituted lobelane analogues was synthesized and evaluated for their [3H]dihydrotetrabenazine binding affinity at the vesicular monoamine transporter and for their inhibition of vesicular [3H]dopamine uptake. Compound 19a, which contains an N-1,2(R)-dihydroxypropyl group, had been identified as a potential clinical candidate for the treatment of methamphetamine abuse.

  我们合成了一系列 N-取代的洛贝兰类似物，并评估了它们在囊泡单胺转运体上的[3H]二氢四苄肼结合亲和力及其对囊泡[3H]多巴胺摄取的抑制作用。化合物 19a 含有一个 N-1,2(R)-二羟基丙基，已被确定为治疗甲基苯丙胺滥用的潜在临床候选药物。
• 2,6-disubstituted piperidines and piperazine compounds
  申请人：——

  公开号：US20040266824A1

  公开（公告）日：2004-12-30

  The present invention is directed to 2,6-disubstituted piperidine and piperazine analogs having the following general formula: 1 which are used to treat diseases of the central nervous system, drug abuse, and withdrawal therefrom as well as treating eating disorders.

  本发明涉及具有以下一般式的2,6-二取代哌啶和哌嗪类似物：1，用于治疗中枢神经系统疾病、药物滥用及其戒断，以及治疗进食障碍。
• US7368443B2
  申请人：——

  公开号：US7368443B2

  公开（公告）日：2008-05-06
• Lobelane analogues as novel ligands for the vesicular monoamine transporter-2
  作者：Guangrong Zheng、Linda P. Dwoskin、Agripina G. Deaciuc、Jun Zhu、Marlon D. Jones、Peter A. Crooks

  DOI：10.1016/j.bmc.2005.04.013

  日期：2005.6

  A series of lobelane analogues has been synthesized and their structure-activity relationships at the vesicular monoamine transporter-2 (VMAT2) have been evaluated. The most potent analogues in this series were the cis-2,6-piperidino analogues, 25b, 27b, 28b, and 30b, with K-i ranging from 430 to 580 nM.. (c) 2005 Elsevier Ltd. All rights reserved.