4-[3-(三氟甲基)苯基]-2-噻唑羧酸 | 847956-11-0

• 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: 4-[3-(三氟甲基)苯基]-2-噻唑羧酸
• 英文名称: 4-(3-(trifluoromethyl)phenyl)thiazole-2-carboxylic acid
• 英文别名: 4-[3-(trifluoromethyl)phenyl]-1,3-thiazole-2-carboxylic acid
• CAS: 847956-11-0
• 化学式: C₁₁H₆F₃NO₂S
• mdl: MFCD07377547
• 分子量: 273.235
• InChiKey: RFUZJOUSSSAGOB-UHFFFAOYSA-N

物化性质

• 沸点：
  423.7±55.0 °C(Predicted)
• 密度：
  1.489

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-[3-(三氟甲基)苯基]-2-噻唑羧酸 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 4-[3-三氟甲基苯基]噻唑
  参考文献：
  名称：

  Novel series of 3-amino-N-(4-aryl-1,1-dioxothian-4-yl)butanamides as potent and selective dipeptidyl peptidase IV inhibitors

  摘要：

  A series of novel 3-amino-N-(4-aryl-1,1-dioxothian-4-yl)butanamides were investigated as dipeptidyl peptidase IV (DPP-4) inhibitors. Introduction of a 4-phenylthiazol-2-yl group showed highly potent DPP-4 inhibitory activity. Among various derivatives, (3R)-3-amino-N-(4-(4-phenylthiazol-2-yl)-tetrahydro-2H-thiopyran-4-yl)-4-(2,4,5-trifluorophenyl)butanamide 1,1-dioxide (30) reduced blood glucose excursion in an oral glucose tolerance test by oral administration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.099
• 作为产物：
  描述：

  2-溴-1-(3-(三氟甲基)苯基)乙酮 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-[3-(三氟甲基)苯基]-2-噻唑羧酸
  参考文献：
  名称：

  Novel series of 3-amino-N-(4-aryl-1,1-dioxothian-4-yl)butanamides as potent and selective dipeptidyl peptidase IV inhibitors

  摘要：

  A series of novel 3-amino-N-(4-aryl-1,1-dioxothian-4-yl)butanamides were investigated as dipeptidyl peptidase IV (DPP-4) inhibitors. Introduction of a 4-phenylthiazol-2-yl group showed highly potent DPP-4 inhibitory activity. Among various derivatives, (3R)-3-amino-N-(4-(4-phenylthiazol-2-yl)-tetrahydro-2H-thiopyran-4-yl)-4-(2,4,5-trifluorophenyl)butanamide 1,1-dioxide (30) reduced blood glucose excursion in an oral glucose tolerance test by oral administration. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.099

文献信息

• Cyclic derivatives as modulators of chemokine receptor activity
  申请人：Carter H. Percy

  公开号：US20050054627A1

  公开（公告）日：2005-03-10

  The present application describes modulators of MCP-1 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the treatment of rheumatoid arthritis, multiple sclerosis, atherosclerosis and asthma.

  当前申请描述了MCP-1的调节剂，其化学公式为(I):或其药用可接受的盐形式，用于治疗类风湿性关节炎、多发性硬化症、动脉粥样硬化和哮喘。
• Substituted cycloalkylamine derivatives as modulators of chemokine receptor activity
  申请人：Carter H. Percy

  公开号：US20050054626A1

  公开（公告）日：2005-03-10

  The present application describes modulators of MCP-1 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma, multiple sclerosis, artherosclerosis, and rheumatoid arthritis.

  本申请描述了MCP-1的调节剂，化学式为(I)：或其药用可接受的盐形式，用于预防哮喘、多发性硬化症、动脉粥样硬化和类风湿性关节炎。
• CYCLIC DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Carter Percy H.

  公开号：US20090124668A1

  公开（公告）日：2009-05-14

  The present application describes modulators of MCP-1 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the treatment of rheumatoid arthritis, multiple sclerosis, atherosclerosis and asthma.

  本申请描述了 MCP-1 的调节剂，其化学式为 (I) 或其药学上可接受的盐形式，适用于治疗类风湿性关节炎、多发性硬化症、动脉粥样硬化和哮喘。
• Design, synthesis, and evaluation of thiazolecarboxamide derivatives as stimulator of interferon gene inhibitors
  作者：Zechen Jin、Yan Zhang、Xin Luo、Meiyu Geng、Wenhu Duan、Zuoquan Xie、Hefeng Zhang

  DOI：10.1007/s11030-024-10860-6

  日期：2025.2

  Stimulator of interferon gene (STING) plays critical roles in the cytoplasmic DNA-sensing pathway and in the induction of inflammatory response. Aberrant cytoplasmic DNA accumulation and STING activation are implicated in numerous inflammatory and autoimmune diseases. Here, we reported the discovery of a series of thiazolecarboxamide-based STING inhibitors through a molecular planarity/symmetry disruption

  干扰素基因刺激物 (STING) 在细胞质 DNA 传感途径和炎症反应的诱导中发挥着关键作用。异常的细胞质 DNA 积累和 STING 激活与许多炎症和自身免疫性疾病有关。在这里，我们报告了通过分子平面性/对称性破坏策略发现了一系列基于噻唑甲酰胺的 STING 抑制剂。特权化合物15b显着抑制人类和小鼠细胞中的 STING 信号传导并抑制免疫炎症细胞因子水平。体内实验表明， 15b可有效改善 MSA-2 刺激的小鼠和Trex1 -D18N 小鼠中的免疫炎症细胞因子上调。此外，化合物15b在抑制干扰素刺激基因 15 (ISG15) 方面表现出增强的功效，干扰素刺激基因 15 是 STING 的关键正反馈调节因子。总体而言，化合物15b值得进一步开发用于治疗 STING 相关炎症和自身免疫性疾病。  图形概要
• SUBSTITUTED CYCLOALKYAMINE DERIVATIVES AS MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY
  申请人：Bristol-Myers Squibb Company

  公开号：EP1656138A2

  公开（公告）日：2006-05-17