(R)-N-(3,5-bis(trifluoromethyl)benzyl)-2-(2-aminothiazol-4-yl)-4-(4-phenylpiperidin-1-yl)butanamide | 929008-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-N-(3,5-bis(trifluoromethyl)benzyl)-2-(2-aminothiazol-4-yl)-4-(4-phenylpiperidin-1-yl)butanamide
• 英文别名: (2R)-2-(2-amino-1,3-thiazol-4-yl)-N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-4-(4-phenylpiperidin-1-yl)butanamide
• CAS: 929008-09-3
• 化学式: C₂₇H₂₈F₆N₄OS
• 分子量: 570.602
• InChiKey: QMTYTDODWBWULC-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  99.5
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (R)-N-(3,5-bis(trifluoromethyl)benzyl)-2-(2-aminothiazol-4-yl)-4-(4-phenylpiperidin-1-yl)butanamide 、 异氰酸甲酯 以 二氯甲烷 为溶剂， 生成 (R)-1-(4-(1-(3,5-bis(trifluoromethyl)benzylamino)-1-oxo-4-(4-phenylpiperidin-1-yl)butan-2-yl)thiazol-2-yl)-3-methylurea
  参考文献：
  名称：

  α-Aminothiazole-γ-aminobutanoic amides as potent, small molecule CCR2 receptor antagonists

  摘要：

  A series of racemic and homochiral alpha-aminothiazole-gamma-aminobutyroamides that display high affinities for human and murine CCR2 and functional antagonism by inhibition of monocyte recruitment are described. A representative example is (2S)2- [2-(acetyl amino)-1, 3-thiazol-4-yl]-N-[3-methyl-5-(trifluoromethyl)benzyl]-4-(4-phenylpiperidin-1-yl)butanamide, which shows 5 nM affinity for human monocytes and CHO cells expressing the human CCR2b receptor. It also inhibited MCP-1 initiated chemotaxis of human monocytes with an IC50 of 0.69 nM. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.059
• 作为产物：
  描述：

  (R)-tert-butyl 4-(1-(3,5-bis(trifluoromethyl)benzylamino)-1-oxo-4-(4-phenylpiperidin-1-yl)butan-2-yl)thiazol-2-ylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-N-(3,5-bis(trifluoromethyl)benzyl)-2-(2-aminothiazol-4-yl)-4-(4-phenylpiperidin-1-yl)butanamide
  参考文献：
  名称：

  α-Aminothiazole-γ-aminobutanoic amides as potent, small molecule CCR2 receptor antagonists

  摘要：

  A series of racemic and homochiral alpha-aminothiazole-gamma-aminobutyroamides that display high affinities for human and murine CCR2 and functional antagonism by inhibition of monocyte recruitment are described. A representative example is (2S)2- [2-(acetyl amino)-1, 3-thiazol-4-yl]-N-[3-methyl-5-(trifluoromethyl)benzyl]-4-(4-phenylpiperidin-1-yl)butanamide, which shows 5 nM affinity for human monocytes and CHO cells expressing the human CCR2b receptor. It also inhibited MCP-1 initiated chemotaxis of human monocytes with an IC50 of 0.69 nM. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.059

文献信息

• α-Aminothiazole-γ-aminobutanoic amides as potent, small molecule CCR2 receptor antagonists
  作者：Changyou Zhou、Liangqin Guo、William H. Parsons、Sander G. Mills、Malcolm MacCoss、Pasquale P. Vicario、Hans Zweerink、Margaret A. Cascieri、Martin S. Springer、Lihu Yang

  DOI：10.1016/j.bmcl.2006.10.059

  日期：2007.1

  A series of racemic and homochiral alpha-aminothiazole-gamma-aminobutyroamides that display high affinities for human and murine CCR2 and functional antagonism by inhibition of monocyte recruitment are described. A representative example is (2S)2- [2-(acetyl amino)-1, 3-thiazol-4-yl]-N-[3-methyl-5-(trifluoromethyl)benzyl]-4-(4-phenylpiperidin-1-yl)butanamide, which shows 5 nM affinity for human monocytes and CHO cells expressing the human CCR2b receptor. It also inhibited MCP-1 initiated chemotaxis of human monocytes with an IC50 of 0.69 nM. (c) 2006 Elsevier Ltd. All rights reserved.