1-(4-(5-((2-氨基噻唑-5-基)硫基)-2-甲氧基-4-甲基苯甲酰基)哌嗪-1-基)乙 | 439578-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-(5-((2-氨基噻唑-5-基)硫基)-2-甲氧基-4-甲基苯甲酰基)哌嗪-1-基)乙
• 英文名称: 1-(4-(5-(2-Aminothiazol-5-ylthio)-2-methoxy-4-methylbenzoyl)piperazin-1-yl)ethanone
• 英文别名: 1-[4-[5-[(2-amino-1,3-thiazol-5-yl)sulfanyl]-2-methoxy-4-methylbenzoyl]piperazin-1-yl]ethanone
• CAS: 439578-98-0
• 化学式: C₁₈H₂₂N₄O₃S₂
• 分子量: 406.53
• InChiKey: FARNTXCAKWOTQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  1-(4-(5-((2-氨基噻唑-5-基)硫基)-2-甲氧基-4-甲基苯甲酰基)哌嗪-1-基)乙 在 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-(5-((5-(4-乙酰基哌嗪-1-甲酰基)-4-甲氧基-2-甲基苯基)硫基)噻唑-2-基)-4-(((3,3-二甲基丁烷-2-基)氨基)甲基)苯甲酰胺
  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-[(5-carbomethoxy-4-methoxy-2-methylphenyl)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 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-(4-(5-((2-氨基噻唑-5-基)硫基)-2-甲氧基-4-甲基苯甲酰基)哌嗪-1-基)乙
  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

• 一种具有酪氨酸激酶抑制活性的噻唑类化合物的合成方法
  申请人：上海皓元化学科技有限公司

  公开号：CN105541751A

  公开（公告）日：2016-05-04

  本发明涉及一种具有酪氨酸激酶抑制活性的噻唑类化合物(I)的合成方法，化合物3与化合物II在缩合剂的作用下反应得到化合物I，该方法简单、收率高、操作简便、后处理简单，利于工业化生产。其中，R为C1～C6的烷基、醇、醚。
• ITK degradation to block T cell receptor signaling and overcome therapeutic resistance in T cell lymphomas
  作者：Baishan Jiang、David M. Weinstock、Katherine A. Donovan、Hong-Wei Sun、Ashley Wolfe、Sam Amaka、Nicholas L. Donaldson、Gongwei Wu、Yuan Jiang、Ryan A. Wilcox、Eric S. Fischer、Nathanael S. Gray、Wenchao Wu

  DOI：10.1016/j.chembiol.2023.03.007

  日期：2023.4
• US7241781B2
  申请人：——

  公开号：US7241781B2

  公开（公告）日：2007-07-10
• US2023/226196
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.