4-(Pyrrolidin-2-yl)benzoic acid | 937685-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 4-(Pyrrolidin-2-yl)benzoic acid
• 英文别名: 4-pyrrolidin-2-ylbenzoic acid
• CAS: 937685-45-5
• 化学式: C₁₁H₁₃NO₂
• mdl: MFCD09036090
• 分子量: 191.23
• InChiKey: AVXHPPWBIQGVBK-UHFFFAOYSA-N

物化性质

• 沸点：
  355.7±35.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2,3-Dihydro-1-benzofuran-5-yl)-2-(2-fluoroanilino)acetic acid 、 4-(Pyrrolidin-2-yl)benzoic acid 在 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 水 、 lithium hydroxide 作用下， 以 二氯甲烷 、 四氢呋喃 、 甲醇 为溶剂， 反应 16.0h， 生成 4-[1-[2-(2,3-Dihydro-1-benzofuran-5-yl)-2-(2-fluoroanilino)acetyl]pyrrolidin-2-yl]benzoic acid
  参考文献：
  名称：

  Arylglycine derivatives as potent transient receptor potential melastatin 8 (TRPM8) antagonists

  摘要：

  A series of arylglycine-based analogs was synthesized and tested for TRPM8 antagonism in a cell-based functional assay. Following structure-activity relationship studies in vitro, a number of compounds were identified as potent TRPM8 antagonists and were subsequently evaluated in an in vivo pharmacodynamic assay of icilin-induced 'wet-dog' shaking in which compound 12 was fully effective. TRPM8 antagonists of the type described here may be useful in treating pain conditions wherein cold hypersensitivity is a dominant feature. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.062

文献信息

• Arylglycine derivatives as potent transient receptor potential melastatin 8 (TRPM8) antagonists
  作者：Bin Zhu、Mingde Xia、Xiaoqing Xu、Donald W. Ludovici、Manomi Tennakoon、Mark A. Youngman、Jay M. Matthews、Scott L. Dax、Raymond W. Colburn、Ning Qin、Tasha L. Hutchinson、Mary Lou Lubin、Michael R. Brandt、Dennis J. Stone、Christopher M. Flores、Mark J. Macielag

  DOI：10.1016/j.bmcl.2013.01.062

  日期：2013.4

  A series of arylglycine-based analogs was synthesized and tested for TRPM8 antagonism in a cell-based functional assay. Following structure-activity relationship studies in vitro, a number of compounds were identified as potent TRPM8 antagonists and were subsequently evaluated in an in vivo pharmacodynamic assay of icilin-induced 'wet-dog' shaking in which compound 12 was fully effective. TRPM8 antagonists of the type described here may be useful in treating pain conditions wherein cold hypersensitivity is a dominant feature. (C) 2013 Elsevier Ltd. All rights reserved.