[1-(3-methylpyridin-2-yl)-3,6-dihydro-2H-pyridin-4-yl] trifluoromethanesulfonate | 1072921-05-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [1-(3-methylpyridin-2-yl)-3,6-dihydro-2H-pyridin-4-yl] trifluoromethanesulfonate
• CAS: 1072921-05-1
• 化学式: C₁₂H₁₃F₃N₂O₃S
• 分子量: 322.308
• InChiKey: DPXLGKDNLQJBFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲醇 、 [1-(3-methylpyridin-2-yl)-3,6-dihydro-2H-pyridin-4-yl] trifluoromethanesulfonate 、 一氧化碳 在 palladium diacetate 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以53%的产率得到methyl 3'-methyl-3,6-dihydro-2H-[1,2'-bipyridine]-4-carboxylate
  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
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 1-(3-甲基吡啶-2-基)哌啶-4-酮 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 生成 [1-(3-methylpyridin-2-yl)-3,6-dihydro-2H-pyridin-4-yl] trifluoromethanesulfonate
  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