3-Hydroxy-2-p-chlorbenzyl-chinoxalin | 93986-07-3

• 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: 3-Hydroxy-2-p-chlorbenzyl-chinoxalin
• 英文别名: 3-[(4-chlorophenyl)methyl]-1H-quinoxalin-2-one
• CAS: 93986-07-3
• 化学式: C₁₅H₁₁ClN₂O
• 分子量: 270.718
• InChiKey: DDCDAAMCQKNJDY-UHFFFAOYSA-N

物化性质

• 溶解度：
  0.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-2-p-chlorbenzyl-chinoxalin 在 chromium(VI) oxide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.0h， 以73%的产率得到3-(4-chlorobenzoyl)-quinoxalin-2(1H)-one
  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：

  3-(α,4-dichlorobenzyl)quinoxalin-2(1H)-one 在 硫脲 、 盐酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 80.0h， 以87%的产率得到3-Hydroxy-2-p-chlorbenzyl-chinoxalin
  参考文献：
  名称：

  3-（α-氯苄基）喹喔啉-2（1H）-one用作合成3-苄基喹喔啉-2（1H）-one和噻唑[3,4-a]喹喔啉-4（5H）-one的多功能试剂。

  摘要：

  通过易于获得的3-（α-氯苄基）的反应合成3-苄基喹喔啉-2（1 H）-one和噻唑并[3,4- a ] quinoxalin-4（5 H）-one的简便有效方法）喹喔啉-2（1 H）-酮和硫脲已被开发出来，后者具有多种作用。讨论了可能的机制。可以单锅方式执行这两个步骤，以中等到高产量生产所需的产品。

  DOI：

  10.1002/jhet.3616

文献信息

• Microwave-Assisted Solvent-Dependent Reaction: Chemoselective Synthesis of Quinoxalin-2(1<i>H</i>)-ones, Benzo[<i>d</i>]imidazoles and Dipeptides
  作者：Shu-Liang Wang、Jie Ding、Bo Jiang、Yuan Gao、Shu-Jiang Tu

  DOI：10.1021/co2001247

  日期：2011.9.12

  A microwave-assisted solvent-dependent chemoselective reaction dealing with 4-arylidene-2-phenyloxazol-5-ones and diverse ortho-diamines to achieve three types of molecular scaffolds, 3-benzylquinoxalin-2(1H)-ones, benzimidazole and β-amino dipeptides is reported. The procedures feature short reaction time, good to excellent yields, operational simplicity, as well as easily available starting materials

  微波辅助溶剂依赖性化学选择性反应，处理4-亚芳基-2-苯基恶唑-5-酮和各种邻二胺以实现三种类型的分子支架，即3-苄基喹喔啉-2（1H）-酮，苯并咪唑和β-报道了氨基二肽。该方法的特点是反应时间短，产率高至优异，操作简便以及易于获得的起始原料。这些化合物对于有机化学和药物化学研究具有重要意义。
• 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.
• Subhashini, N. J. Prameela; Hanumanthu, P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, p. 32 - 35
  作者：Subhashini, N. J. Prameela、Hanumanthu, P.

  DOI：——

  日期：——
• Synthesis of 3-benzyl-2-substituted quinoxalines as novel monoamine oxidase A inhibitors
  作者：Seham Y. Hassan、Sherine N. Khattab、Adnan A. Bekhit、Adel Amer

  DOI：10.1016/j.bmcl.2005.11.088

  日期：2006.3

  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.
• SUBHASHINI, N. J. PRAMEELA;HANUMANTHU, P., INDIAN J. CHEM., 26,(1987) N 1, 32-35
  作者：SUBHASHINI, N. J. PRAMEELA、HANUMANTHU, P.

  DOI：——

  日期：——