4-(4-chloro-3-(trifluoromethyl)phenyl)-1-(2-hydroxy-3-phenoxypropyl)piperidin-4-ol | 1075076-02-6

• 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: 4-(4-chloro-3-(trifluoromethyl)phenyl)-1-(2-hydroxy-3-phenoxypropyl)piperidin-4-ol
• 英文别名: 4-[4-chloro-3-(trifluoromethyl)phenyl]-1-(2-hydroxy-3-phenoxypropyl)piperidin-4-ol
• CAS: 1075076-02-6
• 化学式: C₂₁H₂₃ClF₃NO₃
• 分子量: 429.867
• InChiKey: CZFBPJXRVVEFJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.9
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-[4-氯-3-(三氟甲基)苯基]-4-哌啶醇 、 苯基缩水甘油醚 以 乙醇 为溶剂， 以79.1%的产率得到4-(4-chloro-3-(trifluoromethyl)phenyl)-1-(2-hydroxy-3-phenoxypropyl)piperidin-4-ol
  参考文献：
  名称：

  Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity

  摘要：

  Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 member optimization library was generated using parallel synthesis. Products of this library 1-((R)-3-(4-chlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl) phenyl) piperidin-4-ol and 1-((S)-3-(4-(trifluoromethyl) phenoxy)-2-hydroxypropyl)-4-(4-chloro-3-( trifluoromethyl) phenyl) piperidin-4-ol demonstrated good anti-tuberculosis activity. Unfortunately, side effects were observed upon in vivo anti-tuberculosis testing of these compounds precluding their further advancement, which may be in part due to the secondary pharmacology associated with the aryl piperidinol core. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.04.005

文献信息

• [EN] METHODS OF USING HYDROXYCYCLOHEXANE AND HYDROXYPIPERIDINE COMPOUNDS IN TREATING SODIUM CHANNEL-MEDIATED DISEASES OR CONDITIONS<br/>[FR] PROCÉDÉS DE TRAITEMENT DE MALADIES OU D'AFFECTIONS ASSOCIÉES AUX CANAUX SODIQUES AU MOYEN DE COMPOSÉS D'HYDROXYCYCLOHEXANE ET D'HYDROXYPIPÉRIDINE
  申请人：XENON PHARMACEUTICALS INC

  公开号：WO2008134547A1

  公开（公告）日：2008-11-06

  [EN] This invention is directed to methods of using compounds of formula (I): wherein m, n, A, V, R¹, R², R^2a, R³, R^3a, R⁴, R^4a, R⁵, R^5a and R⁶ are as defined herein, as a stereoisomer, enantiomer, tautomer thereof or mixtures thereof; or a pharmaceutically acceptable salt, solvate or prodrug thereof, for the treatment and/or prevention of sodium channel-mediated diseases or conditions, such as pain.
  [FR] L'invention concerne des procédés d'utilisation de composés de la formule (I) : dans laquelle m, n, A, V, R¹, R², R^2a, R³, R^3a, R⁴, R^4a, R⁵, R^5a et R⁶ sont tels définis ci-dessus, sous la forme d'un stéréo-isomère, énantiomère, tautomère de ceux-ci, ou de mélanges de ceux-ci ; ou un sel, un solvat ou un promédicament pharmaceutiquement acceptable de ceux-ci, pour le traitement et/ou la prévention de maladies ou d'affections associées aux canaux sodiques, comme la douleur.
• Discovery, synthesis, and biological evaluation of piperidinol analogs with anti-tuberculosis activity
  作者：Dianqing Sun、Michael S. Scherman、Victoria Jones、Julian G. Hurdle、Lisa K. Woolhiser、Susan E. Knudson、Anne J. Lenaerts、Richard A. Slayden、Michael R. McNeil、Richard E. Lee

  DOI：10.1016/j.bmc.2009.04.005

  日期：2009.5

  Direct anti-tuberculosis screening of commercially available compound libraries identified a novel piperidinol with interesting anti-tuberculosis activity and drug like characteristics. To generate a structure activity relationship about this hit a 22 member optimization library was generated using parallel synthesis. Products of this library 1-((R)-3-(4-chlorophenoxy)-2-hydroxypropyl)-4-(4-chloro-3-(trifluoromethyl) phenyl) piperidin-4-ol and 1-((S)-3-(4-(trifluoromethyl) phenoxy)-2-hydroxypropyl)-4-(4-chloro-3-( trifluoromethyl) phenyl) piperidin-4-ol demonstrated good anti-tuberculosis activity. Unfortunately, side effects were observed upon in vivo anti-tuberculosis testing of these compounds precluding their further advancement, which may be in part due to the secondary pharmacology associated with the aryl piperidinol core. (C) 2009 Elsevier Ltd. All rights reserved.