1-(4-(5-(2-Aminothiazol-5-ylthio)-2-methylbenzoyl)piperazin-1-yl)ethanone | 903568-40-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-(4-(5-(2-Aminothiazol-5-ylthio)-2-methylbenzoyl)piperazin-1-yl)ethanone
• 英文别名: 1-[4-[5-[(2-amino-1,3-thiazol-5-yl)sulfanyl]-2-methylbenzoyl]piperazin-1-yl]ethanone
• CAS: 903568-40-1
• 化学式: C₁₇H₂₀N₄O₂S₂
• 分子量: 376.503
• InChiKey: VDEUFLSMJCUZSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(4-(5-(2-Aminothiazol-5-ylthio)-2-methylbenzoyl)piperazin-1-yl)ethanone 、 4-二甲氨基苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 N-[5-[[3-[(4-Acetylpiperazin-1-yl)carbonyl]-4-methylphenyl]thio]thiazol-2-yl]-4-(N,N-dimethylamino)benzamide
  参考文献：
  名称：

  Discovery and SAR of 2-amino-5-(thioaryl)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 3 is identified as a potent and selective Itk inhibitor which inhibits anti-TCR antibody induced IL-2 production in mice in vivo and was previously reported to reduce lung inflammation in a mouse model of ovalbumin induced allergy/asthma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.060
• 作为产物：
  描述：

  在 4-二甲氨基吡啶 、 sodium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 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 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-(4-(5-(2-Aminothiazol-5-ylthio)-2-methylbenzoyl)piperazin-1-yl)ethanone
  参考文献：
  名称：

  Discovery and SAR of 2-amino-5-(thioaryl)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 3 is identified as a potent and selective Itk inhibitor which inhibits anti-TCR antibody induced IL-2 production in mice in vivo and was previously reported to reduce lung inflammation in a mouse model of ovalbumin induced allergy/asthma. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.060

文献信息

• Identification of 2-amino-5-(thioaryl)thiazoles as inhibitors of nerve growth factor receptor TrkA
  作者：Soong-Hoon Kim、John S. Tokarski、Kenneth J. Leavitt、Brian E. Fink、Mark E. Salvati、Robert Moquin、Mary T. Obermeier、George L. Trainor、Gregory G. Vite、Linda K. Stadnick、Jonathan S. Lippy、Dan You、Matthew V. Lorenzi、Ping Chen

  DOI：10.1016/j.bmcl.2007.11.076

  日期：2008.1

  2-Amino-5-(thioaryl)thiazoles are potent inhibitors of TrkA (e.g., 20h, TrkA IC50 = 0.6 nM) that show anti-proliferative effect in cellular assays. A proposed inhibitor binding mode to TrkA active site is consistent with key SAR observations. (c) 2007 Elsevier Ltd. All rights reserved.
• Discovery and SAR of 2-amino-5-(thioaryl)thiazoles as potent and selective Itk inhibitors
  作者：Jagabandhu Das、Joseph A. Furch、Chunjian Liu、Robert V. Moquin、James Lin、Steven H. Spergel、Kim W. McIntyre、David J. Shuster、Kathleen D. O’Day、Becky Penhallow、Chen-Yi Hung、Arthur M. Doweyko、Amrita Kamath、Hongjian Zhang、Punit Marathe、Steven B. Kanner、Tai-An Lin、John H. Dodd、Joel C. Barrish、John Wityak

  DOI：10.1016/j.bmcl.2006.04.060

  日期：2006.7

  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 3 is identified as a potent and selective Itk inhibitor which inhibits anti-TCR antibody induced IL-2 production in mice in vivo and was previously reported to reduce lung inflammation in a mouse model of ovalbumin induced allergy/asthma. (c) 2006 Elsevier Ltd. All rights reserved.