2-Chloro-3-(4-chloro-benzyl)-quinoxaline | 881922-66-3

• 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: 2-Chloro-3-(4-chloro-benzyl)-quinoxaline
• 英文别名: 2-chloro-3-[(4-chlorophenyl)methyl]quinoxaline
• CAS: 881922-66-3
• 化学式: C₁₅H₁₀Cl₂N₂
• 分子量: 289.164
• InChiKey: VSODSFUBVZYDEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-Chloro-3-(4-chloro-benzyl)-quinoxaline 在 肼 作用下， 以 异丙醇 为溶剂， 反应 0.25h， 以71.1%的产率得到[3-(4-Chloro-benzyl)-quinoxalin-2-yl]-hydrazine
  参考文献：
  名称：

  Synthesis of 3-benzyl-2-substituted quinoxalines as novel monoamine oxidase A inhibitors

  摘要：

  A new series of 3-benzyl-2-substituted quinoxalines have been synthesized by means of microwave enhancement of nucleophilic substitution reaction involving the corresponding 2-chloroquinoxaline analogs and substituted amines or hydrazine. The synthesized compounds were evaluated for their monoamine oxidase A and B inhibitory activity by determination of their IC50. All the newly synthesized compounds showed more selective inhibitory activity toward NIAO-A than MAO-B. In addition, the acute toxicity of the synthesized compounds was determined. This work may be a fruitful matrix of the synthesis of a new series of novel MAO-A inhibitors with good safety margins. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.088
• 作为产物：
  描述：

  3-Hydroxy-2-p-chlorbenzyl-chinoxalin 在 三氯氧磷 作用下， 反应 2.0h， 以67.7%的产率得到2-Chloro-3-(4-chloro-benzyl)-quinoxaline
  参考文献：
  名称：

  Synthesis of 3-benzyl-2-substituted quinoxalines as novel monoamine oxidase A inhibitors

  摘要：

  A new series of 3-benzyl-2-substituted quinoxalines have been synthesized by means of microwave enhancement of nucleophilic substitution reaction involving the corresponding 2-chloroquinoxaline analogs and substituted amines or hydrazine. The synthesized compounds were evaluated for their monoamine oxidase A and B inhibitory activity by determination of their IC50. All the newly synthesized compounds showed more selective inhibitory activity toward NIAO-A than MAO-B. In addition, the acute toxicity of the synthesized compounds was determined. This work may be a fruitful matrix of the synthesis of a new series of novel MAO-A inhibitors with good safety margins. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.088

文献信息

• Activated carbon/Brønsted acid-promoted aerobic benzylic oxidation under “on-water” condition: Green and efficient synthesis of 3-benzoylquinoxalinones as potent tubulin inhibitors
  作者：Qi Guan、Lin Cong、Qing Wang、Changyue Yu、Kai Bao、Kai Zhou、Lan Wu、Weige Zhang

  DOI：10.1016/j.ejmech.2019.111894

  日期：2020.1

  Green chemistry is becoming the favored approach to preparing drug molecules in pharmaceutical industry. Herein, we developed a clean and efficient method to synthesize 3-benzoylquinoxalines via activated carbon promoted aerobic benzylic oxidation under "on-water" condition. Moreover, biological studies with this class of compounds reveal an antiproliferative profile. Further structure modifications are performed and the investigations exhibited that the most active 12a could inhibit the microtubule polymerization by binding to tubulin and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells, In addition, molecular docking studies allow the rationalization of the pharmacodynamic properties observed. Our systematic studies provide not only guidance for applications of O-2/AC/H2O system, but also a new scaffold targeting tubulin for antitumor agent discovery. (C) 2019 Published by Elsevier Masson SAS.