{5-[3-(4-Acetyl-piperazine-1-carbonyl)-phenylsulfanyl]-thiazol-2-yl}-carbamic acid tert-butyl ester | 439578-80-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: {5-[3-(4-Acetyl-piperazine-1-carbonyl)-phenylsulfanyl]-thiazol-2-yl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[5-[3-(4-acetylpiperazine-1-carbonyl)phenyl]sulfanyl-1,3-thiazol-2-yl]carbamate
• CAS: 439578-80-0
• 化学式: C₂₁H₂₆N₄O₄S₂
• 分子量: 462.594
• InChiKey: YNOVPGUSVDVUJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  {5-[3-(4-Acetyl-piperazine-1-carbonyl)-phenylsulfanyl]-thiazol-2-yl}-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 生成 4-Acetyl-1-[3-[(2-aminothiazol-5-yl)thio]benzoyl]piperazine
  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：

  2-amino-5-[(3-carbomethoxyphenyl)thio]thiazole 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 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 {5-[3-(4-Acetyl-piperazine-1-carbonyl)-phenylsulfanyl]-thiazol-2-yl}-carbamic acid tert-butyl ester
  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

• US7241781B2
  申请人：——

  公开号：US7241781B2

  公开（公告）日：2007-07-10
• 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.