(7-methoxy-3-methyl-1,4-dioxy-quinoxalin-2-yl)-phenyl-methanone | 60680-39-9

• 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-methoxy-3-methyl-1,4-dioxy-quinoxalin-2-yl)-phenyl-methanone
• 英文别名: 1,4-Dihydroxy-7-methoxy-3-methylquinoxalin-2-yl phenyl ketone；(7-methoxy-3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)-phenylmethanone
• CAS: 60680-39-9
• 化学式: C₁₇H₁₄N₂O₄
• 分子量: 310.309
• InChiKey: ROYUBYXRBWLGMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (7-methoxy-3-methyl-1,4-dioxy-quinoxalin-2-yl)-phenyl-methanone 以14%的产率得到
  参考文献：
  名称：

  JARRAR A. A.; HALAWI S. S.; HADDADIN M. J., HETEROCYCLES, 1976, 4, NO 6, 1077-1082

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲氧基苯并呋喃 3-氧化物 、 1-苯基-1,3-丁二酮 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以27%的产率得到(7-methoxy-3-methyl-1,4-dioxy-quinoxalin-2-yl)-phenyl-methanone
  参考文献：
  名称：

  Synthesis of new 2-acetyl and 2-benzoyl quinoxaline 1,4-di-N-oxide derivatives as anti-Mycobacterium tuberculosis agents

  摘要：

  A series of 2-acetyl and 2-benzoyl-6(7)-substituted quinoxaline 1,4-di-N-oxide derivatives were synthesized and evaluated for in vitro antituberculosis activity. The results show that 2-acetyl-3-methylquinoxaline 1,4-di-N-oxide derivatives with chlorine, methyl or methoxy group in position 7 of the benzene moiety (compounds 2, 4 and 6, respectively) and unsubstituted (3) have good antitubercular activity, exhibiting EC90/MIC values between 0.80 and 4.29. In conclusion, the potency, selectivity and low cytotoxicity of these compounds make them valid leads for synthesizing new compounds that possess better activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00137-5

文献信息

• New quinoxaline 1,4-di-N-oxides. Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides
  作者：Kamelia M. Amin、Magda M.F. Ismail、Eman Noaman、Dalia H. Soliman、Yousry A. Ammar

  DOI：10.1016/j.bmc.2006.06.038

  日期：2006.10

  Hypoxic cells which are common feature of solid tumors are resistant to both anticancer drugs and radiation therapy. Thus, the identification of drugs with the selective toxicity toward hypoxic cells is an important target in anticancer chemotherapy. Tirapazamine has been shown to be an efficient and selective cytotoxin after bioreductive activation in hypoxic cells which is thought to be due to the presence of the 1,4-di-N-oxide. A new series of quinoxaline 1,4-di-N-oxides and fused quinoxaline di-N-oxides were synthesized and evaluated for hypoxic-cytotoxic activity on EAC cell line. Compound 10a was the most potent cytotoxin IC50 0.9 mu g/mL, potency 75 mu g/mL, and was approximately 15 times more selective cytotoxin (HCR > 111) than 3-aminoquinoxaline-2-carbonitrile which has been used as a standard (HCR > 7.5). Compounds 4 and 3a,b were more selective than the standard. In addition, antitumor activity against Hepg2 (liver) and U251 (brain) human cell lines was evaluated, compounds 9c and 8a were the most active against Hepg2 with IC50 values 1.9 and 2.9 mu g/mL, respectively, however, all the tested compounds were nontoxic against U251 cell line. (c) 2006 Elsevier Ltd. All rights reserved.