ethyl (E)-3-(2-chloro-5-ethyl-3-pyridyl)-2-propenoate | 1256961-41-7

• 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: ethyl (E)-3-(2-chloro-5-ethyl-3-pyridyl)-2-propenoate
• 英文别名: ethyl (E)-3-(2-chloro-5-ethyl-3-pyridyl)prop-2-enoate；ethyl (E)-3-(2-chloro-5-ethylpyridin-3-yl)prop-2-enoate
• CAS: 1256961-41-7
• 化学式: C₁₂H₁₄ClNO₂
• 分子量: 239.702
• InChiKey: PMVGOVZIMYPICV-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-chloro-5-ethylnicotinaldehyde 、 三氟乙酰乙酸乙酯 在 哌啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以90%的产率得到ethyl (E)-3-(2-chloro-5-ethyl-3-pyridyl)-2-propenoate
  参考文献：
  名称：

  合成（E）-α，β-不饱和酯和酮的新方法

  摘要：

  在哌啶存在下，羰基化合物与4,4,4,4-三氟乙酰乙酸乙酯和三氟取代的1,3-二酮反应，可以实现（E）-α，β-不饱和酯和酮的一般和实用合成在室温（≈40°C）下于二氯甲烷中具有出色的立体选择性（参见方案）。

  DOI：

  10.1002/chem.201000883

文献信息

• Anti-mycobacterial, cytotoxic activities of Knoevenagel and (E)-α,β-unsaturated esters and ketones from 2-chloronicotinaldehydes
  作者：Pathi Suman、Rayala Nageswara Rao、Bhimapaka China Raju、Dharmarajan Sriram、Pulla Venkat Koushik

  DOI：10.1007/s00044-013-0622-4

  日期：2014.1

  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.