(S)-4-(1-fluoro-2-(2-(2,3,6-trifluorophenyl)ethanamido)-ethyl)piperidine-1-carboxylic acid 1-methylcyclopropyl ester | 1280608-09-4

• 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: (S)-4-(1-fluoro-2-(2-(2,3,6-trifluorophenyl)ethanamido)-ethyl)piperidine-1-carboxylic acid 1-methylcyclopropyl ester
• 英文别名: (S)-1-methylcyclopropyl-4-(1-fluoro-2-(2-(2,3,6-trifluorophenyl)ethanoylamino)-ethyl)piperidine-1-carboxylate；(S)-1-methylcyclopropyl 4-(1-fluoro-2-(2-(2,3,6-trifluorophenyl)acetamido)ethyl)piperidine-1-carboxylate；(1-methylcyclopropyl) 4-[(1S)-1-fluoro-2-[[2-(2,3,6-trifluorophenyl)acetyl]amino]ethyl]piperidine-1-carboxylate
• CAS: 1280608-09-4
• 化学式: C₂₀H₂₄F₄N₂O₃
• 分子量: 416.416
• InChiKey: QCIKTRZVLCLGFT-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-(2-氧代乙基)哌啶-1-羧酸叔丁酯 在 sodium tetrahydroborate 、 叠氮磷酸二苯酯 、 10% palladium on activated charcoal 、 氢气 、 (5S)-()-2,2,3-三甲基-5-苄基-4-咪唑啉酮 、 1-羟基苯并三唑 、 N-氟代双苯磺酰胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 生成 (S)-4-(1-fluoro-2-(2-(2,3,6-trifluorophenyl)ethanamido)-ethyl)piperidine-1-carboxylic acid 1-methylcyclopropyl ester
  参考文献：
  名称：

  Design and evaluation of a 2-(2,3,6-trifluorophenyl)acetamide derivative as an agonist of the GPR119 receptor

  摘要：

  The design and synthesis of a GPR119 agonist bearing a 2-(2,3,6-trifluorophenyl)acetamide group is described. The design capitalized on the conformational restriction found in N-beta-fluoroethylamide derivatives to help maintain good levels of potency while driving down both lipophilicity and oxidative metabolism in human liver microsomes. The chemical stability and bioactivation potential are discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.088

文献信息

• [EN] 4- (5-CYANO-PYRAZOL-1-YL) -PIPERIDINE DERIVATIVES AS GPR 119 MODULATORS<br/>[FR] DÉRIVÉS DE 4-(5-CYANOPYRAZOL-1-YL)PIPÉRIDINE EN TANT QUE MODULATEURS DU GPR119
  申请人：PFIZER

  公开号：WO2012069948A1

  公开（公告）日：2012-05-31

  Compounds that modulate the activity of the G-protein-coupled receptor GPR119 and their uses in the treatment of diseases linked to the modulation of the G-protein- coupled receptor GPR119 in animals are described herein.

  本文描述了调节G蛋白偶联受体GPR119活性的化合物及其在治疗与动物中G蛋白偶联受体GPR119调节相关疾病中的用途。
• [EN] GPR 119 MODULATORS<br/>[FR] MODULATEURS DE GPR 119
  申请人：PFIZER

  公开号：WO2013011402A1

  公开（公告）日：2013-01-24

  Compounds that modulate the activity of the G-protein-coupled receptor GPR119 and their uses in the treatment of diseases linked to the modulation of the G-protein- coupled receptor GPR119 in animals are described herein.

  本文描述了调节G蛋白偶联受体GPR119活性的化合物及其在治疗与动物中G蛋白偶联受体GPR119调节相关的疾病中的用途。
• 4- (5-CYANO-PYRAZOL-1-YL) -PIPERIDINE DERIVATIVES AS GPR 119 MODULATORS
  申请人：Pfizer Inc.

  公开号：EP2643310A1

  公开（公告）日：2013-10-02
• GPR 119 MODULATORS
  申请人：Pfizer Inc.

  公开号：EP2731944A1

  公开（公告）日：2014-05-21
• Design and evaluation of a 2-(2,3,6-trifluorophenyl)acetamide derivative as an agonist of the GPR119 receptor
  作者：Vincent Mascitti、Benjamin D. Stevens、Chulho Choi、Kim F. McClure、Cristiano R.W. Guimarães、Kathleen A. Farley、Michael J. Munchhof、Ralph P. Robinson、Kentaro Futatsugi、Sophie Y. Lavergne、Bruce A. Lefker、Peter Cornelius、Paul D. Bonin、Amit S. Kalgutkar、Raman Sharma、Yue Chen

  DOI：10.1016/j.bmcl.2011.01.088

  日期：2011.3

  The design and synthesis of a GPR119 agonist bearing a 2-(2,3,6-trifluorophenyl)acetamide group is described. The design capitalized on the conformational restriction found in N-beta-fluoroethylamide derivatives to help maintain good levels of potency while driving down both lipophilicity and oxidative metabolism in human liver microsomes. The chemical stability and bioactivation potential are discussed. (C) 2011 Elsevier Ltd. All rights reserved.