5-(2-Amino-thiazol-5-ylsulfanyl)-2-hydroxy-benzoic acid methyl ester | 903568-15-0

• 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-(2-Amino-thiazol-5-ylsulfanyl)-2-hydroxy-benzoic acid methyl ester
• CAS: 903568-15-0
• 化学式: C₁₁H₁₀N₂O₃S₂
• 分子量: 282.344
• InChiKey: CKCLHMPXTHJYCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  85.44
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-(2-Amino-thiazol-5-ylsulfanyl)-2-hydroxy-benzoic acid methyl ester 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 tert-butyl N-[5-[3-(4-acetylpiperazine-1-carbonyl)-4-hydroxyphenyl]sulfanyl-1,3-thiazol-2-yl]carbamate
  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：

  甲醇 、 2-氨基-5-溴噻唑 、 2-羟基-5-硫烷基苯甲酸 在 sodium methylate 、 盐酸 作用下， 以 甲醇 、 1,4-二氧六环 为溶剂， 生成 5-(2-Amino-thiazol-5-ylsulfanyl)-2-hydroxy-benzoic acid methyl 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