methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate

• 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-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate
• 英文别名: methyl (2R)-2-[[5-(4-aminophenyl)-1,3-thiazole-2-carbonyl]amino]-3-methylbutanoate
• 化学式: C₁₆H₁₉N₃O₃S
• 分子量: 333.411
• InChiKey: LIOGKYZIJHDLDW-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(5-(4-aminophenyl)thiazole-2-carboxamido)-3-methylbutanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 32.0h， 生成 3-methyl-2-(5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)thiazole-2-carboxamido)butanoic 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：

  2-氨基-1-(4-硝基苯基)乙酮盐酸盐 在 劳森试剂 、 N-甲基吗啉 、 水 、 铁粉 、 氯化铵 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 乙酸乙酯 为溶剂， 反应 7.17h， 生成 methyl 2-(5-(4-aminophenyl)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