methyl 3-(2-chloro-5-methylpyridin-3-yl)-2-cyanoacrylate | 1442435-45-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-(2-chloro-5-methylpyridin-3-yl)-2-cyanoacrylate
• CAS: 1442435-45-1
• 化学式: C₁₁H₉ClN₂O₂
• 分子量: 236.658
• InChiKey: DJRNWHGDELWCSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  62.98
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-氯-5-甲基吡啶-3-甲醛 、 氰乙酸甲酯 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl 3-(2-chloro-5-methylpyridin-3-yl)-2-cyanoacrylate
  参考文献：
  名称：

  Anti-mycobacterial, cytotoxic activities of Knoevenagel and (E)-α,β-unsaturated esters and ketones from 2-chloronicotinaldehydes

  摘要：

  Series of 2-chloronicotinaldehyde Knoevenagel derivatives 3a-r; (E)-alpha,beta-unsaturated esters and ketones 5a-k were prepared and evaluated for their in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H(37)Rv (Mtb). Compounds 3e, 5b, 5d, 5e, 5g and 5i-k were shown potent to significant activity. Compound 5j is the most potent Mtb inhibitor (MIC: 4.89 mu M) when compared to standard drugs Ethambutol (MIC: 7.63 mu M) and Ciprofloxacin (MIC: 9.44 mu M). Eight compounds displayed potent/significant activity against M. tuberculosis were chosen for the cytotoxicity against three cell lines (Raw 264.7, MCF7, and HeLa). Compound 5j displayed low toxicity with high selective index (15-30) and is an interesting new compound may serve for the development of therapeutics targeted against anti-mycobacterial compounds. This is the first report assigning in vitro anti-mycobacterial inhibitory activity and structure-activity relationship for this class of substituted 2-chloronicotinaldehyde derivatives and presents new family of compounds.

  DOI：

  10.1007/s00044-013-0622-4