methyl 2-(4-(4-((6-fluorobenzo[d]thiazol-2-yl)amino)phenyl)thiazole-2-carboxamido)-3-methylbutanoate | 1300747-97-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(4-(4-((6-fluorobenzo[d]thiazol-2-yl)amino)phenyl)thiazole-2-carboxamido)-3-methylbutanoate
• CAS: 1300747-97-0
• 化学式: C₂₃H₂₁FN₄O₃S₂
• 分子量: 484.575
• InChiKey: WXBOBFTWGPRTBL-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  93.21
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-(4-((6-fluorobenzo[d]thiazol-2-yl)amino)phenyl)thiazole-2-carboxamido)-3-methylbutanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以68%的产率得到2-(4-(4-((6-fluorobenzo[d]thiazol-2-yl)amino)phenyl)thiazole-2-carboxamido)-3-methylbutanoic acid
  参考文献：
  名称：

  Evaluation of thiazole containing biaryl analogs as diacylglycerol acyltransferase 1 (DGAT1) inhibitors

  摘要：

  Biphenyl carboxylic acids, exemplified by compound 5, are known potent inhibitors of diacylglycerol acyltransferase, DGAT1, an enzyme involved in the final committed step of triglyceride biosynthesis. We have synthesized and evaluated 2-phenylthiazole, 4-phenylthiazole, and 5-phenylthiazole analogs as DGAT1 inhibitors. The 5-phenylthiazole series exhibited potent DGAT1 inhibition when evaluated using an in vitro enzymatic assay and an in vivo fat tolerance test in mice. Compound 33 (IC50 = 23 nM) exhibiting promising oral pharmacokinetic parameters (AUC(inf) = 7058 ng*h/ml, T-1/2 = 0.83 h) coupled with 87 percent reduction of plasma triglycerides in vivo may serve as a lead for developing newer anti-obesity agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.006
• 作为产物：
  描述：

  4-(4-硝基苯基)-2-噻唑羧酸乙酯 在 N-甲基吗啉 、 盐酸 、 aluminum (III) chloride 、 水 、 铁粉 、 lithium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 正丁醇 为溶剂， 反应 26.33h， 生成 methyl 2-(4-(4-((6-fluorobenzo[d]thiazol-2-yl)amino)phenyl)thiazole-2-carboxamido)-3-methylbutanoate
  参考文献：
  名称：

  Evaluation of thiazole containing biaryl analogs as diacylglycerol acyltransferase 1 (DGAT1) inhibitors

  摘要：

  Biphenyl carboxylic acids, exemplified by compound 5, are known potent inhibitors of diacylglycerol acyltransferase, DGAT1, an enzyme involved in the final committed step of triglyceride biosynthesis. We have synthesized and evaluated 2-phenylthiazole, 4-phenylthiazole, and 5-phenylthiazole analogs as DGAT1 inhibitors. The 5-phenylthiazole series exhibited potent DGAT1 inhibition when evaluated using an in vitro enzymatic assay and an in vivo fat tolerance test in mice. Compound 33 (IC50 = 23 nM) exhibiting promising oral pharmacokinetic parameters (AUC(inf) = 7058 ng*h/ml, T-1/2 = 0.83 h) coupled with 87 percent reduction of plasma triglycerides in vivo may serve as a lead for developing newer anti-obesity agents. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.006