2-(2-Amino-thiazol-4-yl)-4-(4-benzoimidazol-1-yl-piperidin-1-yl)-N-(3,5-bis-trifluoromethyl-benzyl)-butyramide | 929007-91-0

• 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: 2-(2-Amino-thiazol-4-yl)-4-(4-benzoimidazol-1-yl-piperidin-1-yl)-N-(3,5-bis-trifluoromethyl-benzyl)-butyramide
• 英文别名: 4-(4-(1H-benzo[d]imidazol-1-yl)piperidin-1-yl)-N-(3,5-bis(trifluoromethyl)benzyl)-2-(2-aminothiazol-4-yl)butanamide；2-(2-amino-1,3-thiazol-4-yl)-4-[4-(benzimidazol-1-yl)piperidin-1-yl]-N-[[3,5-bis(trifluoromethyl)phenyl]methyl]butanamide
• CAS: 929007-91-0
• 化学式: C₂₈H₂₈F₆N₆OS
• 分子量: 610.626
• InChiKey: MYYAWMQCERSIHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(2-Amino-thiazol-4-yl)-4-(4-benzoimidazol-1-yl-piperidin-1-yl)-N-(3,5-bis-trifluoromethyl-benzyl)-butyramide 、 乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2-Acetylamino-thiazol-4-yl)-4-(4-benzoimidazol-1-yl-piperidin-1-yl)-N-(3,5-bis-trifluoromethyl-benzyl)-butyramide
  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：

  tert-butyl (2E)-2-[(tert-butoxycarbonyl)inimo]-4-(2-ethoxy-2-oxoethyl)-1,3-thiazole-3-(2H)-carboxylate 在 lithium hydroxide 、 四氧化锇 、 正丁基锂 、 N-甲基吲哚酮 、 三乙酰氧基硼氢化钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 柠檬酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 2-(2-Amino-thiazol-4-yl)-4-(4-benzoimidazol-1-yl-piperidin-1-yl)-N-(3,5-bis-trifluoromethyl-benzyl)-butyramide
  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.