3-(5,6-二甲基-1H-苯并咪唑-2-基)丙酸 | 173737-04-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 3-(5,6-二甲基-1H-苯并咪唑-2-基)丙酸
• 英文名称: 3-(5,6-dimethyl-1H-benzo[d]imidazol-2-yl)propanoic acid
• 英文别名: 3-(5,6-dimethyl-1H-benzimidazol-2-yl)-propionic acid；3-(5,6-Dimethyl-1H-benzimidazol-2-yl)-propionsaeure；3-(5,6-dimethyl-1H-benzimidazol-2-yl)propanoic acid
• CAS: 173737-04-7
• 化学式: C₁₂H₁₄N₂O₂
• mdl: MFCD07186395
• 分子量: 218.255
• InChiKey: KWHVMRSTWKAEKR-UHFFFAOYSA-N

物化性质

• 熔点：
  222-224 °C (decomp)
• 沸点：
  511.0±38.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  4-(2-amino-4,5-dimethylanilino)-4-oxobutanoic acid 在 溶剂黄146 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 3-(5,6-二甲基-1H-苯并咪唑-2-基)丙酸
  参考文献：
  名称：

  Hit-to-Lead Optimization and Discovery of 5-((5-([1,1′-Biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic Acid (MK-3903): A Novel Class of Benzimidazole-Based Activators of AMP-Activated Protein Kinase

  摘要：

  AMP-activated protein kinase (AMPK) plays an essential role as a cellular energy sensor and master regulator of metabolism in eukaryotes. Dysregulated lipid and carbohydrate metabolism resulting from insulin resistance leads to hyperglycemia, the hallmark of type 2 diabetes mellitus (T2DM). While pharmacological activation of AMPK is anticipated to improve these parameters, the discovery of selective, direct activators has proven challenging. We now describe a hit-to-lead effort resulting in the discovery of a potent and selective class of benzimidazole-based direct AMPK activators, exemplified by 5-((5-([1,1'-biphenyl]-4-yl)-6-chloro-1H-benzo[d]imidazol-2-yl)oxy)-2-methylbenzoic acid, 42 (MK-3903). Compound 42 exhibited robust target engagement in mouse liver following oral dosing, leading to improved lipid metabolism and insulin sensitization in mice.

  DOI：

  10.1021/acs.jmedchem.7b01344

文献信息

• Ghosh, Sabari; Hudrlik, Anne; Mukhopadhyay, Chhanda, Journal of the Indian Chemical Society, 2013, vol. 90, # 10, p. 1737 - 1748
  作者：Ghosh, Sabari、Hudrlik, Anne、Mukhopadhyay, Chhanda

  DOI：——

  日期：——
• Lettre et al., Chemische Berichte, 1951, vol. 84, p. 719,727
  作者：Lettre et al.

  DOI：——

  日期：——