1-{4-[5-(2-Amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone | 745074-50-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1-{4-[5-(2-Amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone
• CAS: 745074-50-4
• 化学式: C₁₉H₂₄N₄O₂S₂
• 分子量: 404.557
• InChiKey: QIZLDSXGIDEUQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  79.53
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-{4-[5-(2-Amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone 在 吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 BMS-488516
  参考文献：
  名称：

  Discovery and SAR of 2-amino-5-[(thiomethyl)aryl]thiazoles as potent and selective Itk inhibitors

  摘要：

  A series of structurally novel aminothiazole based small molecule inhibitors of Itk were prepared to elucidate their structure-activity relationships (SARs), selectivity and cell activity in inhibiting IL-2 secretion in a Jurkat T-cell assay. Compound 2 is identified as a potent and selective Ilk inhibitor which inhibits anti-TCR antibody induced IL-2 production in mice in vivo. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.115
• 作为产物：
  描述：

  methyl 5-(chloromethyl)-2,3-dimethylbenzoate 在 N-甲基吗啉 、 sodium hydroxide 、 sodium tetrahydroborate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 1-{4-[5-(2-Amino-thiazol-5-ylsulfanylmethyl)-2,3-dimethyl-benzoyl]-piperazin-1-yl}-ethanone
  参考文献：
  名称：

  Discovery and SAR of 2-amino-5-[(thiomethyl)aryl]thiazoles as potent and selective Itk inhibitors

  摘要：

  A series of structurally novel aminothiazole based small molecule inhibitors of Itk were prepared to elucidate their structure-activity relationships (SARs), selectivity and cell activity in inhibiting IL-2 secretion in a Jurkat T-cell assay. Compound 2 is identified as a potent and selective Ilk inhibitor which inhibits anti-TCR antibody induced IL-2 production in mice in vivo. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.115