5-甲基苯并呋喃-1-氧化物 | 19164-41-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 中文名称: 5-甲基苯并呋喃-1-氧化物
• 中文别名: 5-甲基苯并呋咱-1-氧化物
• 英文名称: 5-methylbenzofuroxan
• 英文别名: 5(6)-methylbenzofurazan N-oxide；5-methyl-benzofuroxan N-oxide；5-methylbenzofurazan 1-oxide；5-methylbenzofurazan-1-oxide；5-methylbenzofuroxane；Benzofurazan, 5-methyl-, 1-oxide；5-methyl-1-oxido-2,1,3-benzoxadiazol-1-ium
• CAS: 19164-41-1
• 化学式: C₇H₆N₂O₂
• mdl: MFCD00068057
• 分子量: 150.137
• InChiKey: HCWVKDOCXDWFEH-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98°C
• 稳定性/保质期：

  常温常压下稳定，避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S22,S24/25
• 海关编码：
  2934999090
• 储存条件：
  常温下应密闭避光保存，并放置在通风干燥处。

反应信息

• 作为反应物：
  描述：

  5-甲基苯并呋喃-1-氧化物 在 硫酸氢铵 、 magnesium 作用下， 以 甲醇 为溶剂， 以80%的产率得到3,4-二氨基甲苯
  参考文献：
  名称：

  硫酸铵 - 镁促进芳香硝基化合物的选择性还原

  摘要：

  摘要 使用新型还原体系 (NH4SO4-Mg/Al/Bi) 将各种硝基芳烃和 2,1,3-苯并恶二唑-1-氧化物选择性地快速还原为相应的氨基和二氨基化合物，收率高。

  DOI：

  10.1080/00397919508011478
• 作为产物：
  描述：

  4-甲基乙酰苯胺 在 盐酸 、 sodium azide 、 硫酸 、 硝酸 、 sodium acetate 、 sodium nitrite 作用下， 以 甲苯 为溶剂， 反应 3.17h， 生成 5-甲基苯并呋喃-1-氧化物
  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

• 4-Cyano-2-oxo-1,2,4-oxadiazolo[2,3-<i>a</i>]quinoxaline 5-<i>N</i>-oxides. New synthetic method and reaction with alcohols. Potential cytotoxic activity
  作者：F. J. Martínez Crespo、J. A. Palop、Y. Sainz、S. Narro、V. Senador、M. González、A. López De Ceráin、A. Monge、E. Hamilton、A. J. Barker

  DOI：10.1002/jhet.5570330620

  日期：1996.11

  Several quinoxaline 1,4-di-N-oxides have been shown to be efficient and selective cytotoxins for hypoxic cells. We present now a series of 4-cyano-2-oxo-1,2,4-oxadiazolo[2,3-a]quinoxaline 5-N-oxides 2a-2k. They were prepared starting from 3-amino-2-quinoxalinecarbonitrile 1,4-di-N-oxides 1a-1k and 2-chloroethyl isocyanate in dry dioxane at 100–110°. A reaction mechanism is proposed. The treatment of

  几种喹喔啉1,4-二-N-氧化物已被证明是低氧细胞的有效和选择性细胞毒素。现在我们介绍一系列的4-氰基-2-氧代-1,2,4-恶二唑并[2,3- a ]喹喔啉5 - N-氧化物2a-2k。它们是在干燥的二恶烷中在100–110°下从3-氨基-2-喹喔啉腈1，a-二-N-氧化物1a-1k和2-氯乙基异氰酸酯开始制备的。提出了一种反应机理。用异氰酸苯酯处理1a得到2a。2c与硅胶反应，得到1c。化合物2a-2g将其在乙醇和2-丙醇存在下加热，得到相应的氨基甲酸酯3a-3g和4a-4g。通过加热1d和氯甲酸乙酯的混合物已经获得了化合物2d。当将氨基甲酸酯3b加热至150°时制备化合物2b。喹喔啉在有氧和低氧细胞中均作为细胞毒性剂进行了测试。最有趣的化合物是3g和4g。
• New analogs of nitrobenzylthioinosine
  申请人：Grünenthal GmbH

  公开号：EP1352910A1

  公开（公告）日：2003-10-15

  This invention relates to new analogs or derivatives of nitrobenzylthioinosine, use of these new analogs of nitrobenzylthioinosine for the treatment of pain and various other diseases as well as pharmaceuticals comprising at least on new analog of nitrobenzylthioinosine.

  这项发明涉及新的硝基苯基硫基核苷类似物或衍生物，以及利用这些新的硝基苯基硫基核苷类似物治疗疼痛和其他各种疾病，以及包含至少一种新的硝基苯基硫基核苷类似物的药品。
• Synthesis and some properties of 2 H -benzimidazole 1,3-dioxides
  作者：Elena Chugunova、Vladimir Samsonov、Tatiana Gerasimova、Tatiana Rybalova、Irina Bagryanskaya

  DOI：10.1016/j.tet.2015.03.096

  日期：2015.9

  The synthesis of novel 2H-benzimidazole 1,3-dioxides on the basis of benzofuroxans interaction with alcohols in acids is described. The formation of a stable secondary carbocation from alcohol is necessary for formation of 2H-benzimidazole 1,3-dioxide while substituents in benzofuroxans don't prevent the reaction. Under heating 2H-benzimidazole 1,3-dioxides are rearranged to 3H-[2,1,4]benzoxadiazine

  描述了基于苯并呋喃类与酸中的醇相互作用的新型2 H-苯并咪唑1,3-二氧化物的合成。由醇形成稳定的仲碳阳离子对于形成2 H-苯并咪唑1,3-二氧化物是必要的，而苯并呋喃类中的取代基不会阻止反应。在加热下，将2 H-苯并咪唑1，3-二氧化物重排为3 H- [2,1,4]苯并恶二嗪4-氧化物，其稳定性取决于芳环中的取代基。在辐射下，恶二嗪被转化回2 H-苯并咪唑1，3-二氧化物。
• [EN] DRUGS DERIVED FROM DICLOFENAC CONTAINING NO-DONOR HETEROCYCLES, COMPOSITION AND METHOD OF INFLAMMATION TREATMENT<br/>[FR] MEDICAMENTS DERIVES DU DICLOFENAC, CONTENANT DES HETEROCYCLES DONNEURS DE NO, COMPOSITION ET METHODE DE TRAITEMENT DES INFLAMMATIONS
  申请人：CMAX OTIMIZACAO DE RESULTADOS

  公开号：WO2006042387A1

  公开（公告）日：2006-04-27

  The present invention refers to drugs resulting from the pharmaceutical substance diclofenac, relative to the formula. The invention further refers to a pharmaceutical composition, which involves the said drugs and a pharmaceutically adequate vehicle. It is also described a method for the treatment of inflammation through the administration of the new drugs in patients with gastric problems or subjected to long-term treatments.

  本发明涉及与制药物质双氯芬酸有关的药物，相对于该化学式。该发明还涉及一种制药组合物，其中包括所述药物和药学上适当的载体。还描述了一种通过在患有胃部问题或接受长期治疗的患者中施用新药物来治疗炎症的方法。
• Synthesis and pharmacological characterization of a novel nitric oxide-releasing diclofenac derivative containing a benzofuroxan moiety
  作者：Paulo Sérgio de Carvalho、Marta Maróstica、Alessandra Gambero、José Pedrazzoli

  DOI：10.1016/j.ejmech.2010.02.034

  日期：2010.6

  [2-(2,6-dichloro-phenylamino)-phenyl]-acetate, a new diclofenac derivative bearing a benzofuroxan heterocyclic moiety in its structure, was prepared by the reaction of sodium diclofenac and 5-bromomethyl-benzo[1,2,5]oxadiazole 1-oxide. Pharmacological characterization of this modified diclofenac maintained the anti-inflammatory activity similar to its parent compound assayed in vitro and in vivo. The

  制备了1-氧-苯并[1,2,5]恶二唑-5-基甲基[2-（2,6-二氯-苯基氨基）-苯基]-乙酸酯，一种新的双氯芬酸衍生物，其结构中带有苯并呋喃基杂环部分双氯芬酸钠和5-溴甲基-苯并[1,2,5]恶二唑1-氧化物的反应。这种修饰的双氯芬酸的药理学特性与其体外和体内测定的母体化合物保持相似的抗炎活性。尽管抑制了前列腺素E 2的胃内含量，但用该修饰化合物未观察到天然双氯芬酸的致溃疡性质。更好的胃耐受性似乎与一氧化氮释放能力有关。

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