4-甲氧基-2,6-二硝基苯胺 | 5350-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲氧基-2,6-二硝基苯胺
• 英文名称: 4-amino-1-methoxy-3,5-dinitrobenzene
• 英文别名: 4-methoxy-2,6-dinitro-aniline；4-Methoxy-2,6-dinitro-anilin；2.6-Dinitro-p-anisidin；3.5-Dinitro-4-amino-phenol-methylaether；3.5-Dinitro-4-amino-anisol；4-methoxy-2,6-dinitro-phenylamine；p-Anisidine, 2,6-dinitro-；4-methoxy-2,6-dinitroaniline
• CAS: 5350-56-1
• 化学式: C₇H₇N₃O₅
• 分子量: 213.15
• InChiKey: GZZJZWYIOOPHOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-甲氧基-2,6-二硝基苯胺 在 ammonium hydroxide 、 硫化氢 作用下， 生成 5-methoxy-3-nitrobenzene-1,2-diamine
  参考文献：
  名称：

  Syntheses in the Quinoxaline Series. Preparation of 7-Methoxy-5-aminoquinoxaline and 7-Methoxy-5-hydroxylaminoquinoxaline

  摘要：

  DOI：

  10.1021/ja01226a009
• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 硫酸 、 硝酸 作用下， 反应 1.58h， 生成 4-甲氧基-2,6-二硝基苯胺
  参考文献：
  名称：

  Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides

  摘要：

  Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy. Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy. The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells. Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and/or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells. Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced. Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxides have reduction potentials significantly more positive than Tirapazamine (E(pc)-0.90 V). The most potent cytotoxins to cells in culture were the 6,7,-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine. The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity. Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro. In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine. This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.

  DOI：

  10.1021/jm00010a023

文献信息

• Methods for preparing 5- and 6-benzyl-functionalized quinoxalines
  申请人：——

  公开号：US20030166934A1

  公开（公告）日：2003-09-04

  The present invention pertains to methods for preparing 5- and 6-benzyl functionalized quinoxalines. In a first embodiment, the method comprises contacting an aqueous suspension of a 5- and 6-halomethyl quinoxaline with a water-soluble nucleophile. In a second embodiment, the method comprises contacting a 5- and 6-halomethyl quinoxaline with an organic solvent-soluble nucleophile in an inert polar organic solvent. In a third embodiment, the method comprises contacting a 5- and 6-halomethyl quinoxaline in an organic solvent with an aqueous solution of a water-soluble nucleophile in the presence of a phase transfer catalyst.

  本发明涉及制备5-和6-苄基功能化喹喔啉的方法。在第一实施例中，该方法包括将5-和6-卤代甲基喹喔啉的水悬浮液与水溶性亲核试剂接触。在第二实施例中，该方法包括将5-和6-卤代甲基喹喔啉与惰性极性有机溶剂中的有机溶剂可溶性亲核试剂接触。在第三实施例中，该方法包括将5-和6-卤代甲基喹喔啉在有机溶剂中与水溶性亲核试剂的水溶液在相转移催化剂的存在下接触。
• Arylpiperazinyl-cyclohexyl indole derivatives for the treatment of depression
  申请人：American Home Products Corporation

  公开号：US20020045628A1

  公开（公告）日：2002-04-18

  Compounds are provided which are useful for the treatment of serotonin-affected neurological disorders which comprise 1 Wherein: R 1 , R 2 and R 3 are each, independently, hydrogen, halogen, CF 3 , alkyl, alkoxy, MeSO 2 , or together can form a 5-7 membered carbocyclic or heterocyclic ring; R 4 is hydrogen, halogen, or alkyl; R 5 is hydrogen, alkyl, alkylaryl, or aryl; R 6 is hydrogen, halogen, CF 3 , CN, carbamide, or alkoxy; X 1 , X 2 and X 3 are each carbon or one of X 1 , X 2 or X 3 may be nitrogen; Y is carbon or nitrogen; and Z is carbon or nitrogen; or pharmaceutically acceptable salts thereof;

  提供了化合物，用于治疗受血清素影响的神经系统疾病，其中包括：1。其中：R1、R2和R3各自独立地为氢、卤素、CF3、烷基、烷氧基、MeSO2，或共同形成5-7个成员的碳环或杂环；R4为氢、卤素或烷基；R5为氢、烷基、烷基芳基或芳基；R6为氢、卤素、 、CN、碳酰胺或烷氧基；X1、X2和X3各自为碳或其中一个为氮；Y为碳或氮；Z为碳或氮；或其药物可接受的盐。
• Methods for preparing 5- and 6-benzyl functionalized quinoxalines
  申请人：AIR PRODUCTS AND CHEMICALS, INC.

  公开号：EP1279668A1

  公开（公告）日：2003-01-29

  The present invention pertains to methods for preparing 5- and 6-benzyl functionalized quinoxalines. In a first embodiment, the method comprises contacting an aqueous suspension of a 5- and 6-halomethyl quinoxaline with a water-soluble nucleophile. In a second embodiment, the method comprises contacting a 5- and 6-halomethyl quinoxaline with an organic solvent-soluble nucleophile in an inert polar organic solvent. In a third embodiment, the method comprises contacting a 5- and 6-halomethyl quinoxaline in an organic solvent with an aqueous solution of a water-soluble nucleophile in the presence of a phase transfer catalyst.

  本发明涉及制备 5-和 6-苄基官能化喹喔啉的方法。在第一个实施方案中，该方法包括将 5-和 6-苄基喹喔啉的水悬浮液与水溶性亲核剂接触。在第二个实施方案中，该方法包括在惰性极性有机溶剂中使 5-和 6-卤甲基喹喔啉与有机溶剂可溶性亲核剂接触。在第三个实施方案中，该方法包括在相转移催化剂存在下，使有机溶剂中的 5-和 6-卤代甲基喹喔啉与水溶性亲核剂的水溶液接触。
• Onys'ko, P. P.; Proklina, N. V.; Prokopenko, V. P., Journal of general chemistry of the USSR, 1984, vol. 54, # 2, p. 289 - 296
  作者：Onys'ko, P. P.、Proklina, N. V.、Prokopenko, V. P.、Gololobov, Yu. G.

  DOI：——

  日期：——
• Galliani, Guido; Rindone, Bruno, Journal of the Chemical Society. Perkin transactions I, 1980, p. 828 - 832
  作者：Galliani, Guido、Rindone, Bruno

  DOI：——

  日期：——

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