N-(4-tert-Butylphenyl)-1-(3-fluoropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxamide | 1072920-99-0

• 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: N-(4-tert-Butylphenyl)-1-(3-fluoropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxamide
• 英文别名: N-(4-tert-butylphenyl)-1-(3-fluoropyridin-2-yl)-3,6-dihydro-2H-pyridine-4-carboxamide
• CAS: 1072920-99-0
• 化学式: C₂₁H₂₄FN₃O
• 分子量: 353.439
• InChiKey: ICKPAMYXVUHXSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3'-fluoro-3,6-dihydro-2H-[1,2']bipyridinyl-4-carboxylic acid 、 4-叔丁基苯胺 在 草酰氯 、 N,N-二甲基甲酰胺 、 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 N-(4-tert-Butylphenyl)-1-(3-fluoropyridin-2-yl)-1,2,3,6-tetrahydropyridine-4-carboxamide
  参考文献：
  名称：

  Tetrahydropyridine-4-carboxamides as novel, potent transient receptor potential vanilloid 1 (TRPV1) antagonists

  摘要：

  A series of 1,2,3,6-tetrahydropyridyl-4-carboxamides, exemplified by 6, have been synthesized and evaluated for in vitro TRPV1 antagonist activity, and in vivo analgesic activity in animal pain models. The tetrahydropyridine 6 is a novel TRPV1 receptor antagonist that potently inhibits receptor-mediated Ca2+ influx in vitro induced by several agonists, including capsaicin, N-arachidonoyldopamine (NADA), and low pH. This compound penetrates the CNS and shows potent anti-nociceptive effects in a broad range of animal pain models upon oral dosing due in part to its ability to antagonize both central and peripheral TRPV1 receptors. The SAR leading to the discovery of 6 is presented in this report. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.005

文献信息

• Tetrahydropyridine-4-carboxamides as novel, potent transient receptor potential vanilloid 1 (TRPV1) antagonists
  作者：Brian S. Brown、Ryan Keddy、Guo Zhu Zheng、Robert G. Schmidt、John R. Koenig、Heath A. McDonald、Bruce R. Bianchi、Prisca Honore、Michael F. Jarvis、Carol S. Surowy、James S. Polakowski、Kennan C. Marsh、Connie R. Faltynek、Chih-Hung Lee

  DOI：10.1016/j.bmc.2008.08.005

  日期：2008.9

  A series of 1,2,3,6-tetrahydropyridyl-4-carboxamides, exemplified by 6, have been synthesized and evaluated for in vitro TRPV1 antagonist activity, and in vivo analgesic activity in animal pain models. The tetrahydropyridine 6 is a novel TRPV1 receptor antagonist that potently inhibits receptor-mediated Ca2+ influx in vitro induced by several agonists, including capsaicin, N-arachidonoyldopamine (NADA), and low pH. This compound penetrates the CNS and shows potent anti-nociceptive effects in a broad range of animal pain models upon oral dosing due in part to its ability to antagonize both central and peripheral TRPV1 receptors. The SAR leading to the discovery of 6 is presented in this report. (C) 2008 Elsevier Ltd. All rights reserved.