2-(2-Fluoro-phenylamino)-1-[(2S)-2-(2-fluoro-phenyl)-pyrrolidin-1-yl]-2-(4-trifluoromethyl-phenyl)-ethanone | 1210855-07-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2-Fluoro-phenylamino)-1-[(2S)-2-(2-fluoro-phenyl)-pyrrolidin-1-yl]-2-(4-trifluoromethyl-phenyl)-ethanone
• 英文别名: 2-(2-fluoroanilino)-1-[(2S)-2-(2-fluorophenyl)pyrrolidin-1-yl]-2-[4-(trifluoromethyl)phenyl]ethanone
• CAS: 1210855-07-4
• 化学式: C₂₅H₂₁F₅N₂O
• 分子量: 460.447
• InChiKey: YAADCCLDXBJNOI-NQCNTLBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(2-Fluoro-phenylamino)-1-[(2S)-2-(2-fluoro-phenyl)-pyrrolidin-1-yl]-2-(4-trifluoromethyl-phenyl)-ethanone 生成 (2R)-2-(2-fluoroanilino)-1-[(2S)-2-(2-fluorophenyl)pyrrolidin-1-yl]-2-[4-(trifluoromethyl)phenyl]ethanone 、 (2S)-2-(2-fluoroanilino)-1-[(2S)-2-(2-fluorophenyl)pyrrolidin-1-yl]-2-[4-(trifluoromethyl)phenyl]ethanone
  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
• 作为产物：
  描述：

  methyl 2-(4-(trifluoromethyl)phenyl)acetate 在 N-溴代丁二酰亚胺(NBS) 、 水 、 氢溴酸 、 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 37.0h， 生成 2-(2-Fluoro-phenylamino)-1-[(2S)-2-(2-fluoro-phenyl)-pyrrolidin-1-yl]-2-(4-trifluoromethyl-phenyl)-ethanone
  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

• Cold Menthol Receptor Antagonists
  申请人：Colburn Raymond W.

  公开号：US20100048589A1

  公开（公告）日：2010-02-25

  Disclosed are compounds, compositions and methods for treating various diseases, syndromes, conditions and disorders, including pain. Such compounds are represented by Formula I as follows: wherein A, B, L, Q, R 1 , R 2 , and R 3 are defined herein.

  揭示了用于治疗各种疾病、综合症、症状和障碍的化合物、组合物和方法，包括疼痛。这些化合物由以下的化学式 I 表示：其中 A、B、L、Q、R1、R2 和 R3 在此处定义。
• COLD MENTHOL RECEPTOR ANTAGONISTS
  申请人：Janssen Pharmaceutica, N.V.

  公开号：EP2331499A1

  公开（公告）日：2011-06-15
• US8143259B2
  申请人：——

  公开号：US8143259B2

  公开（公告）日：2012-03-27
• US8324217B2
  申请人：——

  公开号：US8324217B2

  公开（公告）日：2012-12-04
• [EN] COLD MENTHOL RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DES RÉCEPTEURS AU FROID ACTIVÉS PAR LE MENTHOL
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2010021878A1

  公开（公告）日：2010-02-25

  Disclosed are compounds, compositions and methods for treating various diseases, syndromes, conditions and disorders, including pain. Such compounds are represented by Formula (I), as follows: wherein A, B, L, Q, R1, R2, and R3 are defined herein.