(+)-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methylsulfanyl]acetic acid methyl ester | 807342-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (+)-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methylsulfanyl]acetic acid methyl ester
• 英文别名: methyl 2-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methylsulfanyl]acetate
• CAS: 807342-26-3
• 化学式: C₁₅H₂₀ClNO₂S
• 分子量: 313.848
• InChiKey: QJCSFENQSHMLKU-TZMCWYRMSA-N

物化性质

• 沸点：
  428.1±45.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methylsulfanyl]acetic acid methyl ester 在 氨 作用下， 以 叔丁醇 为溶剂， 反应 72.0h， 以90%的产率得到(+)-2-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methylsulfanyl]acetamide
  参考文献：
  名称：

  [EN] DOPAMINE-, NOREPINEPHRINE- AND SEROTONIN- TRANSPORTER- SELECTIVE HETEROCYCLIC COMPOUNDS AND THEIR THERAPEUTIC APPLICATIONS
  [FR] COMPOSES HETEROCYCLIQUES SELECTIFS VIS-A-VIS DES TRANSPORTEURS DE LA DOPAMINE, DE LA NOREPINEPHRINE ET DE LA SEROTONINE ET LEURS APPLICATIONS THERAPEUTIQUES

  摘要：

  公开号：

  WO2005041875A3
• 作为产物：
  描述：

  (+)-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]acetic acid methyl ester 在 1-氯乙基氯甲酸酯 、 1,8-双二甲氨基萘 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以80%的产率得到(+)-[[(3R,4S)-4-(4-chlorophenyl)piperidin-3-yl]methylsulfanyl]acetic acid methyl ester
  参考文献：
  名称：

  Piperidine-Based Nocaine/Modafinil Hybrid Ligands as Highly Potent Monoamine Transporter Inhibitors:  Efficient Drug Discovery by Rational Lead Hybridization

  摘要：

  Some piperidine-based nocaine/modafinil hybrid ligands have been designed, synthesized, and found to display an improved potency at all three monoamine transporters and particularly for DAT and/or NET. Some highly active and selective monoamine transporter inhibitors with low nanomolar to subnanomolar potency were identified. Ligands of this type may find important applications as positron emission tomography imaging tools and in the treatment of central nervous system disorders such as depression and sleep apnea.

  DOI：

  10.1021/jm040117o

文献信息

• Piperidine-Based Nocaine/Modafinil Hybrid Ligands as Highly Potent Monoamine Transporter Inhibitors:  Efficient Drug Discovery by Rational Lead Hybridization
  作者：Jia Zhou、Rong He、Kenneth M. Johnson、Yanping Ye、Alan P. Kozikowski

  DOI：10.1021/jm040117o

  日期：2004.11.1

  Some piperidine-based nocaine/modafinil hybrid ligands have been designed, synthesized, and found to display an improved potency at all three monoamine transporters and particularly for DAT and/or NET. Some highly active and selective monoamine transporter inhibitors with low nanomolar to subnanomolar potency were identified. Ligands of this type may find important applications as positron emission tomography imaging tools and in the treatment of central nervous system disorders such as depression and sleep apnea.
• DOPAMINE-, NOREPINEPHRINE- AND SEROTONIN- TRANSPORTER- SELECTIVE HETEROCYCLIC COMPOUNDS AND THEIR THERAPEUTIC APPLICATIONS
  申请人：GEORGETOWN UNIVERSITY

  公开号：EP1680113A2

  公开（公告）日：2006-07-19
• Dopamine-, Norepinephrine- and Serotonin- Transporter-Selective Heterocyclic Compounds and Their Therapeutic Applications
  申请人：Kozikowski P. Alan

  公开号：US20070254918A1

  公开（公告）日：2007-11-01

  One aspect of the invention relates to piperidine compounds that are useful as inhibitors of monoamine transporters. The invention also relates to pharmaceutical compositions, comprising a piperidine compound of the invention. Another aspect of the present invention relates to the use of the aforementioned compounds in a method of treating a disorder of the central nervous system in a mammal.
• US8153657B2
  申请人：——

  公开号：US8153657B2

  公开（公告）日：2012-04-10
• Development of new brain imaging agents based upon nocaine–modafinil hybrid monoamine transporter inhibitors
  作者：John L. Musachio、Jinsoo Hong、Masanori Ichise、Nicholas Seneca、Amira K. Brown、Jeih-San Liow、Christer Halldin、Robert B. Innis、Victor W. Pike、Rong He、Jia Zhou、Alan P. Kozikowski

  DOI：10.1016/j.bmcl.2006.03.066

  日期：2006.6

  C-11-labeled (+)-trans-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]ethanol ([C-11]5) and (+)-trans-2-[[(3R,4S)-4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfanyl]-1-(piperidin-1-yl)ethanone ([C-11]6) were synthesized and evaluated as new imaging agents for the norepinephrine transporter (NET). [C-11]5 and [C-11]6 display high affinity for the NET in vitro (K-i = 0.94 and 0.68 nM, respectively) and significant selectivity over the dopamine (DAT) and serotonin transporters (SERT). Because of their high affinity and favorable transporter selectivities we speculated that these ligands might serve as useful PET agents for imaging NET in vivo. Contrary to our expectations, both of these ligands provided brain images that were more typical of those shown by agents binding to the DAT. (c) 2006 Elsevier Ltd. All rights reserved.