5-甲氧基苯并呋喃-1-氧化物 | 7791-49-3

• 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-甲氧基苯并呋喃-1-氧化物
• 中文别名: 5-甲氧基苯并呋咱-1-氧化物
• 英文名称: 5-methoxy-benzo[1,2,5]oxadiazole 1-oxide
• 英文别名: 5-methoxybenzofurazan N-oxide；5-methoxy-benzofuroxan N-oxide；5-Methoxybenzofurazan-1-oxide；5-methoxy-1-oxido-2,1,3-benzoxadiazol-1-ium
• CAS: 7791-49-3
• 化学式: C₇H₆N₂O₃
• mdl: MFCD00068052
• 分子量: 166.136
• InChiKey: ABSKHUSUHODMEL-UHFFFAOYSA-N

物化性质

• 熔点：
  115-118°C
• 沸点：
  291.2±32.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)
• 稳定性/保质期：

  避免接触强氧化剂和强酸。

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S22,S24/25
• 海关编码：
  2934999090
• 储存条件：
  将其存放在阴凉、干燥的紧密容器中。

反应信息

• 作为反应物：
  描述：

  5-甲氧基苯并呋喃-1-氧化物 在 亚磷酸三乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 5-甲氧基苯并呋喃
  参考文献：
  名称：

  铜催化苯并恶二唑与二芳基碘鎓盐的π-核演化，用于区域选择性合成吩嗪骨架。

  摘要：

  由苯并恶二唑和二芳基碘鎓盐实现了铜催化的吩嗪N-氧化物的区域选择性合成。该过程通过苯并恶二唑与二芳基碘鎓盐的亲电芳基化反应开始，然后进行苯并环化反应。容易将原位N-氧化物进一步还原为吩嗪支架并偏离有机荧光材料。

  DOI：

  10.1021/acs.orglett.8b01748
• 作为产物：
  描述：

  4-甲氧基-2-硝基乙酰苯胺 在 盐酸 、 sodium azide 、 硫酸 、 sodium acetate 、 sodium nitrite 作用下， 以 甲苯 为溶剂， 反应 2.5h， 生成 5-甲氧基苯并呋喃-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

• The reactions of benzofuroxan with carbonyl compounds on the surface of solid catalysts
  作者：Tohru Takabatake、Yumiko Hasegawa、Minoru Hasegawa

  DOI：10.1002/jhet.5570300602

  日期：1993.12

  The cyclocondensations of benzofuroxan 1a with carbonyl compounds were smoothly and efficiently carried out by the adsorption of the components on the surface of silica gel or a molecular sieve to form a 2,3-disubstituted quinoxaline 1,4-dioxide. When the reactions using a molecular sieve 3A (powder) were carried out at 90°, the actual reaction times were reduced to 0.5-2 hours. Although Duerckheimer

  通过将组分吸附在硅胶或分子筛的表面上以形成2，3-二取代的喹喔啉1，4-二氧化物，苯并呋喃喃1a与羰基化合物的环缩反应可以平稳有效地进行。当在90°下使用分子筛3A（粉末）进行反应时，实际反应时间减少到0.5-2小时。尽管Duerckheimer报告了当使5-甲氧基苯并呋喃1e与乙酰乙酸乙酯2j反应时仅分离出7-取代的喹喔啉1,4-二氧化物，但通过我们的方法，它仅生成了6-甲氧基异构体作为反应产物。5-羧基苯并呋喃聚糖1f不与羰基化合物反应。
• 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。
• 3-Trifluoromethylquinoxaline <i>N</i>,<i>N</i>′-Dioxides as Anti-Trypanosomatid Agents. Identification of Optimal Anti-<i>T. cruzi</i> Agents and Mechanism of Action Studies
  作者：Diego Benitez、Mauricio Cabrera、Paola Hernández、Lucía Boiani、María L. Lavaggi、Rossanna Di Maio、Gloria Yaluff、Elva Serna、Susana Torres、María E. Ferreira、Ninfa Vera de Bilbao、Enrique Torres、Silvia Pérez-Silanes、Beatriz Solano、Elsa Moreno、Ignacio Aldana、Adela López de Ceráin、Hugo Cerecetto、Mercedes González、Antonio Monge

  DOI：10.1021/jm2002469

  日期：2011.5.26

  For a fourth approach of quinoxaline N,N′-dioxides as anti-trypanosomatid agents against T. cruzi and Leishmania, we found extremely active derivatives. The present study allows us to state the correct requirements for obtaining optimal in vitro anti-T. cruzi activity. Derivatives possessing electron-withdrawing substituents in the 2-, 3-, 6-, and 7-positions were the most active compounds. With regard

  对于喹喔啉N，N'-二氧化物作为抗锥虫和利什曼原虫的抗锥虫病药物的第四种方法，我们发现了活性极高的衍生物。本研究使我们能够阐明获得最佳体外抗T. cruzi活性的正确要求。在2-，3-，6-和7-位具有吸电子取代基的衍生物是活性最高的化合物。考虑到这些特征并考虑到它们的哺乳动物细胞毒性，一些三氟甲基喹喔啉N，N有人提议将二氧化物作为进一步临床研究的候选药物。因此，使用最有前途的衍生物进行了诱变性和体内分析。此外，关于作用机理的研究，已证明线粒体脱氢酶参与了活性最高的衍生物的抗克氏锥虫活性。
• Synthesis of Quinoxaline 1,4-di-N-Oxide Analogues and Crystal Structure of 2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide
  作者：Yingjun Xu、Fanhong Wu、Zhiyi Yao、Minmin Zhang、Sheng Jiang

  DOI：10.3390/molecules16086894

  日期：——

  A series of quinoxaline 1,4-di-N-oxide analogues were prepared from benzofurazan N-oxide derivatives and β-diketone ester compounds by the improved Beirut reaction. The structures of the target products were characterized by NMR, MS, IR and elemental analysis measurements, and that of 2-carbomethoxy-3-hydroxyquinoxaline- di-N-oxide was further confirmed by single-crystal X-ray diffraction. Its crystal

  以苯并呋喃氮氧化物衍生物和β-二酮酯化合物为原料，通过改进的贝鲁特反应制备了一系列喹喔啉1,4-二-N-氧化物类似物。目标产物的结构通过NMR、MS、IR和元素分析测量进行表征，并且通过单晶X射线衍射进一步证实了2-carbomethoxy-3-hydroxyquinoxaline-di-N-oxide的结构。其晶体结构属于单斜晶系，空间群C2/c，a = 14.4320 (12) Å, b = 10.7514 (9) Å, c = 13.2728 (11) Å, V = 1958.5 (3) Å 3, Z = 8. X 射线晶体学分析表明，喹喔啉 1,4-二-N-氧化物表现出 acyloin-endiol 互变异构现象。
• Quinoxalino[2,3-<i>c</i>]cinnolines and Their 5-<i>N</i>-Oxide: Alkoxylation of Methyl-Substituted Quinoxalino[2,3-<i>c</i>]cinnolines to Acetals and Orthoesters
  作者：Makhluf J. Haddadin、Mirna El-Khatib、Tharallah A. Shoker、Christine M. Beavers、Marilyn M. Olmstead、James C. Fettinger、Kelli M. Farber、Mark J. Kurth

  DOI：10.1021/jo201687x

  日期：2011.10.21

  We report the alkoxylation of methyl-substituted quinoxalino[2,3-c]cinnolines to give acetals and orthoesters in high yields. Routes to the precursors of this alkoxylation reaction as well as other quinoxalino[2,3-c]cinnoline and their 5-oxide derivatives are reported. Most of these quinoxalino[2,3-c]cinnolines were prepared by cyclization of the corresponding 2-amino-3-(2-nitrophenyl)quinoxaline,

  我们报告甲基取代的喹喔啉[2,3- c ] cinnolines的烷氧基化以高收率得到乙缩醛和原酸酯。据报道，该烷氧基化反应的前体以及其他喹喔啉[2,3- c ] cinnoline及其5-氧化物衍生物的途径。这些喹喔啉[2,3- c ]喹啉中的大多数是通过相应的2-氨基-3-（2-硝基苯基）喹喔啉的环化反应制备的，这反过来又是苯并呋喃山氧化物加2-硝基苄基氰化物引起的异常贝鲁特反应的结果。 。提出了这些有趣反应的机械解释。

表征谱图