3-(4-methoxybenzoyl)-quinoxalin-2(1H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-methoxybenzoyl)-quinoxalin-2(1H)-one
• 英文别名: 3-(4-methoxybenzoyl)-1H-quinoxalin-2-one
• 化学式: C₁₆H₁₂N₂O₃
• 分子量: 280.283
• InChiKey: GDCWPYSXCOWEBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methoxybenzoyl)-quinoxalin-2(1H)-one 在 copper(l) iodide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  自由基介导的喹喔啉酮远程迁移

  摘要：

  本文公开了自由基介导的喹喔啉酮远程迁移的第一个例子。烯烃的喹喔啉基官能化使用喹喔啉酮取代的叔双烯丙基醇作为底物，通过分子内 1,4-喹喔啉酮迁移进行，并产生复杂的 γ-喹喔啉酮取代的脂肪族酮。一组外部基团与此方法兼容。该方案具有官能团宽泛、对各种外部自由基适应性好、产物多样性高等特点，为喹喔啉酮衍生物的合成打开了一扇新的大门。

  DOI：

  10.1039/d2cc06887g
• 作为产物：
  描述：

  4-[(4-methoxyphenyl)methylene]-2-methyl-5(4H)-oxazolone 在 氧气 、 三氟乙酸 作用下， 以 水 、 乙二醇 为溶剂， 反应 4.0h， 生成 3-(4-methoxybenzoyl)-quinoxalin-2(1H)-one
  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

• Metal-free C3–H acylation of quinoxalin-2(1<i>H</i>)-ones with α-oxo-carboxylic acids
  作者：Hangcheng Ni、Xingzi Shi、Yu Li、Xiaoning Zhang、Jingwei Zhao、Fei Zhao

  DOI：10.1039/d0ob01423k

  日期：——

  Direct C3–H acylation of quinoxalin-2(1H)-ones with α-oxocarboxylic acids under thermo conditions promoted by PIDA has been achieved in a moderate to good yield in a very fast manner.

  在PIDA促进下，在热力条件下，将α-酮羧酸直接酰基化到喹啉-2(1H)-酮上，以中等至良好的产率非常快速地实现。
• 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。
• Intramolecular oxidative rearrangement: I2/TBHP/DMSO-mediated metal free facile access to quinoxalinone derivatives
  作者：Nancy Slathia、Annah Gupta、Kamal K. Kapoor

  DOI：10.1016/j.tetlet.2021.153268

  日期：2021.8

  Iodine/TBHP/DMSO mediated oxidative rearrangement of 3-styrylquinoxalin-2(1H)-one led to the formation of 3-aroylquinoxalin-2(1H)-ones in good to high yields via Kornblum oxidation. This methodology proceeds under mild conditions via oxidative aryl migration, followed by CC bond cleavage and does not make use of any metal.

  碘/TBHP/DMSO 介导的 3-styrylquinoxalin-2( 1H )-one氧化重排导致通过Kornblum 氧化以良好到高产率形成 3-aroylquinoxalin-2( 1H ) -one 。该方法在温和条件下通过氧化芳基迁移进行，然后是 C C 键断裂，并且不使用任何金属。
• 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.
• Radical-mediated remote migration of quinoxalinones
  作者：Chenyang Chang、Qi Zhang、Xinxin Wu、Chen Zhu

  DOI：10.1039/d2cc06887g

  日期：——

  first example of radical-mediated remote migration of quinoxalinones. The quinoxalinonyl-functionalization of alkenes employs the quinoxalinone-substituted tertiary bishomoallylic alcohols as substrates, proceeds through intramolecular 1,4-quinoxalinone migration, and gives rise to complex γ-quinoxalinone-substituted aliphatic ketones. A set of external radicals is compatible with this method. The protocol

  本文公开了自由基介导的喹喔啉酮远程迁移的第一个例子。烯烃的喹喔啉基官能化使用喹喔啉酮取代的叔双烯丙基醇作为底物，通过分子内 1,4-喹喔啉酮迁移进行，并产生复杂的 γ-喹喔啉酮取代的脂肪族酮。一组外部基团与此方法兼容。该方案具有官能团宽泛、对各种外部自由基适应性好、产物多样性高等特点，为喹喔啉酮衍生物的合成打开了一扇新的大门。