allyl 6,7-dichloro-3-methylquinoxaline-2-carboxylate 1,4-dioxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: allyl 6,7-dichloro-3-methylquinoxaline-2-carboxylate 1,4-dioxide
• 英文别名: Prop-2-enyl 6,7-dichloro-3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-carboxylate
• 化学式: C₁₃H₁₀Cl₂N₂O₄
• 分子量: 329.139
• InChiKey: MPFZCKDAKDLQAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰乙酸烯丙酯 、 5,6-dichlorobenzofuroxan 在 三乙胺 作用下， 反应 24.0h， 以7%的产率得到allyl 6,7-dichloro-3-methylquinoxaline-2-carboxylate 1,4-dioxide
  参考文献：
  名称：

  Synthesis of New Quinoxaline-2-carboxylate 1,4-Dioxide Derivatives as Anti-Mycobacterium tuberculosis Agents

  摘要：

  Twenty-nine new 6(7)-substituted quinoxaline-2-carboxylate 1,4-dioxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. In general, the in vitro activity is significantly affected by substituents on the quinoxaline nucleus. It has been observed that the presence of a chloro, methyl, or methoxy group in position 7 of the benzene moiety reduces the MIC and IC50 values. However, antituberculosis activity principally depends on the substituents in the carboxylate group, improving in the following order: benzyl > ethyl > 2-methoxyethyl > allyl > tert-butyl. Fourteen compounds have been selected for macrophage assay, and the results show that ethyl and benzyl 3-methylquinoxaline-2-carboxylate 1,4-dioxide derivatives with the chlorine group in position 7 of the benzene moiety (compounds 10 and 26) and the unsubstituted derivatives (compounds 11 and 27) have good antitubercular activity, including activity in macrophages. In addition, compounds 7 and 28 (the only ones tested up to now) are active against drug-resistant strains of M. tuberculosis H(37)Rv. In conclusion, the potency, selectivity, and low cytotoxicity of these compounds make them valid leads for synthesizing new compounds that possess better activity.

  DOI：

  10.1021/jm049952w

文献信息

• Synthesis of New Quinoxaline-2-carboxylate 1,4-Dioxide Derivatives as Anti-<i>Mycobacterium </i><i>t</i><i>uberculosis</i> Agents
  作者：Andrés Jaso、Belén Zarranz、Ignacio Aldana、Antonio Monge

  DOI：10.1021/jm049952w

  日期：2005.3.1

  Twenty-nine new 6(7)-substituted quinoxaline-2-carboxylate 1,4-dioxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. In general, the in vitro activity is significantly affected by substituents on the quinoxaline nucleus. It has been observed that the presence of a chloro, methyl, or methoxy group in position 7 of the benzene moiety reduces the MIC and IC50 values. However, antituberculosis activity principally depends on the substituents in the carboxylate group, improving in the following order: benzyl > ethyl > 2-methoxyethyl > allyl > tert-butyl. Fourteen compounds have been selected for macrophage assay, and the results show that ethyl and benzyl 3-methylquinoxaline-2-carboxylate 1,4-dioxide derivatives with the chlorine group in position 7 of the benzene moiety (compounds 10 and 26) and the unsubstituted derivatives (compounds 11 and 27) have good antitubercular activity, including activity in macrophages. In addition, compounds 7 and 28 (the only ones tested up to now) are active against drug-resistant strains of M. tuberculosis H(37)Rv. In conclusion, the potency, selectivity, and low cytotoxicity of these compounds make them valid leads for synthesizing new compounds that possess better activity.