7-chloro-3-methyl-1,4-dioxy-quinoxaline-2-carboxylic acid hydrazide | 33433-33-9

• 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: 7-chloro-3-methyl-1,4-dioxy-quinoxaline-2-carboxylic acid hydrazide
• 英文别名: 6-chloro-3-(hydrazinecarbonyl)-2-methylquinoxaline1,4-dioxide
• CAS: 33433-33-9
• 化学式: C₁₀H₉ClN₄O₃
• 分子量: 268.659
• InChiKey: VRBFWLGXWPRGOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  109.0
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-chloro-3-methyl-1,4-dioxy-quinoxaline-2-carboxylic acid hydrazide 在 溶剂黄146 、 sodium nitrite 作用下， 以75%的产率得到7-Chloro-3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-carbonyl azide
  参考文献：
  名称：

  New quinoxaline 1, 4-di-N-oxides: Anticancer and hypoxia-selective therapeutic agents

  摘要：

  A new series of quinoxaline 1,4-di-N-oxides was synthesized and evaluated for antitumor and hypoxic-selective cytotoxic activities. Antitumor activity against liver carcinoma (Hepg2) and brain tumor (U251) human cell lines were evaluated, among the tested compounds, 5b and 9b exhibited potential cytotoxic effect against Hepg2 with IC50 values of 0.77 and 0.50 mu g/mL respectively, whereas, all the tested compounds lack antitumor activity against U251 human cell line. Moreover, compound 4 was the most potent hypoxia selective-cytotoxin on EAC cell line; IC50 2.5 mu g/mL, potency 22 mu g/mL, and was approximately 5.4-times more selective cytotoxin (HCR > 40) than 3-amino-2-quinoxalinecarbonitrile 1,4-dioxide (standard, HCR > 7.4). Compounds 8b and 9b were more selective than the standard. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.02.052
• 作为产物：
  描述：

  6-chloro-3-(ethoxycarbonyl)-2-methylquinoxaline1,4-dioxide 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以56%的产率得到7-chloro-3-methyl-1,4-dioxy-quinoxaline-2-carboxylic acid hydrazide
  参考文献：
  名称：

  Synthesis and Characterization of Newly Fused 1,2-Dihydropyrido[3,4-b], Bridged Oxadiazol-2-yl, 4-Substituted-benzylidene Hydrazide and Arylidene 6-Chloroquinoxaline 1,4-Dioxides

  摘要：

  Some simple reactions using commercially available chemicals were used in the preparation of new biologically remarkable quinoxaline 1,4-dioxide derivatives. Several steps performed on 4-chloro-2-nitroaniline resulted in a quinoxaline 1,4-dioxide derivative, which reacted with dimethylformamide dimethylacetal (DMF-DMA) to produce an enamine. Transamination of this enamine with anilines gave the fused 1,2-dihydropyrido[3,4-b] quinoxaline 5,10-dioxide derivatives via an addition-elimination mechanism. Basic condensation reaction of quinoxaline active methyl afforded unexpected decarboxylated arylidene derivatives by using different aromatic aldehydes. Bridged oxadiazol-2-yl derivatives were obtained from the reaction of a hydrazide derivative with carbon disulfide and p-nitrobenzoic acid respectively. Whereas, acidic condensation of that hydrazide with aromatic aldehydes afforded the arylidene hydrazides.

  DOI：

  10.21577/0103-5053.20180081