2-chloro-3-(4-methoxybenzoyl)quinoxaline | 23773-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-3-(4-methoxybenzoyl)quinoxaline
• 英文别名: 2-Chlor-3-anisoyl-chinoxalin；(3-chloro-quinoxalin-2-yl)-(4-methoxy-phenyl)-methanone；(3-Chloroquinoxalin-2-yl)-(4-methoxyphenyl)methanone
• CAS: 23773-95-7
• 化学式: C₁₆H₁₁ClN₂O₂
• 分子量: 298.729
• InChiKey: RWOXHLLUYTUJGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-甲氧基苯基)哌嗪 、 2-chloro-3-(4-methoxybenzoyl)quinoxaline 反应 2.5h， 以40%的产率得到(4-Methoxy-phenyl)-{3-[4-(4-methoxy-phenyl)-piperazin-1-yl]-quinoxalin-2-yl}-methanone
  参考文献：
  名称：

  新型3-苯甲酰基-2-哌嗪基喹喔啉衍生物可作为潜在的抗肿瘤药

  摘要：

  合成了一系列新的苯甲酰基喹喔啉衍生物（7-26），并评估了在贝塞斯达NCI对一组60种人类细胞系的抗肿瘤活性。在通过初步筛选的化合物中，化合物23在100-10μM时表现出最佳的分布和生长抑制活性。然后测试化合物对叶酸依赖性酶生物文库的影响，包括10μM的胸苷酸合酶和人二氢叶酸还原酶。大多数化合物对所有或部分测试的酶表现出中等抑制活性，可检测的抑制常数（K i）值在0.6-70μM的范围内。化合物21、23、24显示K i hDHFR和hTS均在10-38μM的范围内。

  DOI：

  10.1002/jhet.5570430304
• 作为产物：
  描述：

  2-Chlor-3-(4-methoxy-benzyl)-chinoxalin 在 氧气 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 4.0h， 以75%的产率得到2-chloro-3-(4-methoxybenzoyl)quinoxaline
  参考文献：
  名称：

  Activated carbon/Brønsted acid-promoted aerobic benzylic oxidation under “on-water” condition: Green and efficient synthesis of 3-benzoylquinoxalinones as potent tubulin inhibitors

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2019.111894

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.
• Novel 3-benzoyl-2-piperazinylquinoxaline derivatives as potential antitumor agents
  作者：Sandra Piras、Mario Loriga、Antonio Carta、Giuseppe Paglietti、M. Paola Costi、Stefania Ferrari

  DOI：10.1002/jhet.5570430304

  日期：2006.5

  A series of new benzoylquinoxaline derivatives (7-26) was synthesized and evaluated for antitumor activity against a panel of 60 human cell lines at the NCI of Bethesda. Among the compounds which have passed the preliminary screening, compound 23 exhibited the best profile and growth inhibition activity at 100 - 10 μM. The compounds were then tested towards a folate-dependent enzymes bio-library including

  合成了一系列新的苯甲酰基喹喔啉衍生物（7-26），并评估了在贝塞斯达NCI对一组60种人类细胞系的抗肿瘤活性。在通过初步筛选的化合物中，化合物23在100-10μM时表现出最佳的分布和生长抑制活性。然后测试化合物对叶酸依赖性酶生物文库的影响，包括10μM的胸苷酸合酶和人二氢叶酸还原酶。大多数化合物对所有或部分测试的酶表现出中等抑制活性，可检测的抑制常数（K i）值在0.6-70μM的范围内。化合物21、23、24显示K i hDHFR和hTS均在10-38μM的范围内。