1-(3-phenylpropyl)-piperidin-4-ol | 1226163-73-0

• 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: 1-(3-phenylpropyl)-piperidin-4-ol
• 英文别名: 4-hydroxy(3-phenylpropyl)-piperidine；1-(3-Phenylpropyl)-4-piperidinol；1-(3-phenylpropyl)piperidin-4-ol
• CAS: 1226163-73-0
• 化学式: C₁₄H₂₁NO
• mdl: MFCD16152987
• 分子量: 219.327
• InChiKey: DQMITGUZEYCJIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(R)-(3-(R)-formyl-4-(S)-phenylpyrrolidin-1-yl)-3-methylbutanoic acid,benzyl ester 、 1-(3-phenylpropyl)-piperidin-4-ol 以31 mg (67%)的产率得到2-(R)-(3-(S)-((4-Hydroxy-4-(3-phenylpropyl)piperidin-1-yl)methyl)-4-(S)-phenylpyrrolidin-1-yl)-3-methylbutanoic acid, benzyl ester
  参考文献：
  名称：

  Pyrrolidine modulators of chemokine receptor activity

  摘要：

  本发明涉及式1的吡咯烷化合物：（其中R1、R2、R3、R4、R5、R6和n在此处定义），这些化合物可用作趋化因子受体活性的调节剂。具体来说，这些化合物可用作趋化因子受体CCR-5和/或CCR-3的调节剂。

  公开号：

  US06265434B1
• 作为产物：
  描述：

  4-羟基哌啶 、 1-溴-3-苯基丙烷 在 N,N-二异丙基乙胺 作用下， 反应 1.33h， 以58%的产率得到1-(3-phenylpropyl)-piperidin-4-ol
  参考文献：
  名称：

  Structure–activity relationship exploration of Kv1.3 blockers based on diphenoxylate

  摘要：

  Diphenoxylate, a well-known opioid agonist and anti-diarrhoeal agent, was recently found to block Kv1.3 potassium channels, which have been proposed as potential therapeutic targets for a range of autoimmune diseases. The molecular basis for this Kv1.3 blockade was assessed by the selective removal of functional groups from the structure of diphenoxylate as well as a number of other structural variations. Removal of the nitrile functional group and replacement of the C-4 piperidinyl substituents resulted in several compounds with submicromolar IC50 values. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.080

文献信息

• Design and Synthesis of New Bifunctional Sigma-1 Selective Ligands with Antioxidant Activity
  作者：O. Prezzavento、E. Arena、C. Parenti、L. Pasquinucci、G. Aricò、G. M. Scoto、S. Grancara、A. Toninello、S. Ronsisvalle

  DOI：10.1021/jm3017893

  日期：2013.3.28

  Herein we report the synthesis of new bifunctional sigma-1 (sigma(1))-selective ligands with antioxidant activity. To achieve this goal, we combined the structure of lipoic acid, a universal antioxidant, with an appropriate sigma aminic moiety. Ligands 14 and 26 displayed high affinity and selectivity for sigma(1) receptors (K-i sigma(1) = 1.8 and 5.5 nM; K-i sigma(2)/sigma(1) = 354 and 414, respectively). Compound 26 exhibited in vivo antiopioid effects on kappa opioid (KOP) receptor-mediated analgesia. In rat liver and brain mitochondria (RLM, RBM), this compound significantly reduced the swelling and the oxidation of thiol groups induced by calcium ions. Our results demonstrate that the tested compound has protective effects against oxidative stress.
• US4886813A
  申请人：——

  公开号：US4886813A

  公开（公告）日：1989-12-12
• US6265434B1
  申请人：——

  公开号：US6265434B1

  公开（公告）日：2001-07-24
• [EN] CYCLOPENTYL MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY<br/>[FR] MODULATEURS CYCLOPENTYLE DE L'ACTIVITE DES RECEPTEURS DE LA CHIMIOKINE
  申请人：MERCK & CO INC

  公开号：WO2000076511A1

  公开（公告）日：2000-12-21

  The present invention is directed to compounds of formula (I): (wherein R?1, R2, R3, R7, R8¿, X, Y, Z, x and y are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.
• Pyrrolidine modulators of chemokine receptor activity
  申请人：Merck & Co., Inc.

  公开号：US06265434B1

  公开（公告）日：2001-07-24

  The present invention is directed to pyrrolidine compounds of the formula 1: (wherein R1, R2, R3, R4, R5, R6 and n are defined herein) which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptors CCR-5 and/or CCR-3.

  本发明涉及式1的吡咯烷化合物：（其中R1、R2、R3、R4、R5、R6和n在此处定义），这些化合物可用作趋化因子受体活性的调节剂。具体来说，这些化合物可用作趋化因子受体CCR-5和/或CCR-3的调节剂。