2,4-dimethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester | 34760-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: 2,4-dimethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester
• 英文别名: 2,4-dimethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester
• CAS: 34760-57-1
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: DMWHUOYLDJXXRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2,4-dimethyl-N-(4-(4-(4-(trifluoromethoxy)phenyl)piperidin-1-yl)benzyl)pyrazolo[1,5-a]pyridine-3-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Pyrazolo[1,5-a]pyridine-3-carboxamides as Novel Antitubercular Agents

  摘要：

  A series of pyrazolo[1,5-a]pyridine-3-carboxamide derivatives were designed and synthesized as new anti-Mycobacterium tuberculosis (Mtb) agents. The compounds exhibit promising in vitro potency with nanomolar MIC values against the drug susceptive H37Rv strain and a panel of clinically isolated multidrug-resistant Mtb (MDR-TB) strains. One of the representative compounds (5k) significantly reduces the bacterial burden in an autoluminescent H37Ra infected mouse model, suggesting its promising potential to be a lead compound for future antitubercular drug discovery.

  DOI：

  10.1021/acsmedchemlett.5b00176
• 作为产物：
  描述：

  3-甲基吡啶 、 2-丁炔酸乙酯 在 2,4-二硝基苯基羟胺 、 potassium carbonate 作用下， 以 乙腈 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 2,6-Dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester 、 2,4-dimethyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Pyrazolo[1,5-a]pyridine-3-carboxamides as Novel Antitubercular Agents

  摘要：

  A series of pyrazolo[1,5-a]pyridine-3-carboxamide derivatives were designed and synthesized as new anti-Mycobacterium tuberculosis (Mtb) agents. The compounds exhibit promising in vitro potency with nanomolar MIC values against the drug susceptive H37Rv strain and a panel of clinically isolated multidrug-resistant Mtb (MDR-TB) strains. One of the representative compounds (5k) significantly reduces the bacterial burden in an autoluminescent H37Ra infected mouse model, suggesting its promising potential to be a lead compound for future antitubercular drug discovery.

  DOI：

  10.1021/acsmedchemlett.5b00176