3-[2-amino-5-(phenylcarbonyl)-1,3-thiazol-4-yl]benzoate | 1552267-94-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[2-amino-5-(phenylcarbonyl)-1,3-thiazol-4-yl]benzoate
• CAS: 1552267-94-3
• 化学式: C₁₇H₁₂N₂O₃S
• 分子量: 324.36
• InChiKey: ILMCJMKLDYRNRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.28
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(4-(乙基磺酰基)苯基)乙酸 、 3-[2-amino-5-(phenylcarbonyl)-1,3-thiazol-4-yl]benzoate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以22%的产率得到3-(5-benzoyl-2-(2-(4-(ethylsulfonyl)phenyl)acetamido)thiazol-4-yl)benzoic acid
  参考文献：
  名称：

  Discovery of novel N-(5-(arylcarbonyl)thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl)amides as potent RORγt inhibitors

  摘要：

  Novel series of N-(5-(arylcarbonyl) thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl) amides were discovered as potent retinoic acid receptor-related orphan receptor-gamma-t (ROR gamma t) inhibitors. SAR studies of the ROR gamma t HTS hit 6a led to identification of thiazole ketone amide 8h and thiophene ketone amide 9g with high binding affinity and inhibitory activity of Th17 cell differentiation. Compound 8h showed in vivo efficacy in both mouse experimental autoimmune encephalomyelitis (EAE) and collagen induced arthritis (CIA) models via oral administration. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.021
• 作为产物：
  描述：

  3-[Bis[(4-methoxyphenyl)methyl]carbamothioylcarbamoyl]benzoic acid 在 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-[2-amino-5-(phenylcarbonyl)-1,3-thiazol-4-yl]benzoate
  参考文献：
  名称：

  Discovery of novel N-(5-(arylcarbonyl)thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl)amides as potent RORγt inhibitors

  摘要：

  Novel series of N-(5-(arylcarbonyl) thiazol-2-yl)amides and N-(5-(arylcarbonyl)thiophen-2-yl) amides were discovered as potent retinoic acid receptor-related orphan receptor-gamma-t (ROR gamma t) inhibitors. SAR studies of the ROR gamma t HTS hit 6a led to identification of thiazole ketone amide 8h and thiophene ketone amide 9g with high binding affinity and inhibitory activity of Th17 cell differentiation. Compound 8h showed in vivo efficacy in both mouse experimental autoimmune encephalomyelitis (EAE) and collagen induced arthritis (CIA) models via oral administration. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.021