3-(5-{[(2-methylphenyl)amino]carbonyl}-1,3,4-thiadiazol-2-yl)propanoic acid

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(5-{[(2-methylphenyl)amino]carbonyl}-1,3,4-thiadiazol-2-yl)propanoic acid
• 英文别名: 3-[5-[(2-methylphenyl)carbamoyl]-1,3,4-thiadiazol-2-yl]propanoic acid
• 化学式: C₁₃H₁₃N₃O₃S
• mdl: MFCD12028290
• 分子量: 291.331
• InChiKey: AMVBJNASGDTSAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氯-N-(2-甲基苯基)乙酰胺 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 一水合肼 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 3-(5-{[(2-methylphenyl)amino]carbonyl}-1,3,4-thiadiazol-2-yl)propanoic acid
  参考文献：
  名称：

  Novel agonists of free fatty acid receptor 1 (GPR40) based on 3-(1,3,4-thiadiazol-2-yl)propanoic acid scaffold

  摘要：

  1,3,4-Thiadiazole was explored as a more polar, heterocyclic replacement for the phenyl ring in the 3-arylpropionic acid pharmacophore present in the majority of GPR40 agonists. Out of 13 compounds synthesized using a flexible, three-step protocol (involving no chromatographic purification), four compounds were confirmed to activate the target in micromolar concentration range. While the potency of the series should be subject of further optimization, the remarkable aqueous solubility and microsomal stability observed for the lead compound (8g) apparently attests to this new scaffold's high promise in the GPR40 agonist field.

  DOI：

  10.3109/14756366.2016.1142984

文献信息

• Novel agonists of free fatty acid receptor 1 (GPR40) based on 3-(1,3,4-thiadiazol-2-yl)propanoic acid scaffold
  作者：Mikhail Krasavin、Alexey Lukin、Nikolay Zhurilo、Alexey Kovalenko、Ihor Zahanich、Sergey Zozulya

  DOI：10.3109/14756366.2016.1142984

  日期：2016.11.1

  1,3,4-Thiadiazole was explored as a more polar, heterocyclic replacement for the phenyl ring in the 3-arylpropionic acid pharmacophore present in the majority of GPR40 agonists. Out of 13 compounds synthesized using a flexible, three-step protocol (involving no chromatographic purification), four compounds were confirmed to activate the target in micromolar concentration range. While the potency of the series should be subject of further optimization, the remarkable aqueous solubility and microsomal stability observed for the lead compound (8g) apparently attests to this new scaffold's high promise in the GPR40 agonist field.