5-氯苯并呋喃 | 17348-69-5

• 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-氯苯并呋喃
• 中文别名: 5-氯苯并呋噁
• 英文名称: 5-chlorobenzofurazan-1-oxide
• 英文别名: 5-chlorobenzofuroxan；5-Chlorbenzofuroxan；5-Chlorobenzofurazan 1-oxide；5-chloro-1-oxido-2,1,3-benzoxadiazol-1-ium
• CAS: 17348-69-5
• 化学式: C₆H₃ClN₂O₂
• mdl: MFCD00068063
• 分子量: 170.555
• InChiKey: DHPQXIQZZCNOLI-UHFFFAOYSA-N

物化性质

• 熔点：
  45-48°C
• 沸点：
  287.1±32.0 °C(Predicted)
• 密度：
  1.61 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-氯苯并呋喃 在 硫酸 、 硝酸 作用下， 以 乙醇 为溶剂， 生成 4-methylamino-7-nitro-2,1,3-benzoxadiazole
  参考文献：
  名称：

  潜在的抗白血病和免疫抑制药物。一些苯并-2,1,3-恶二唑（苯并呋喃）及其N-氧化物（苯并呋喃）的制备及其体外药理活性。

  摘要：

  DOI：

  10.1021/jm00308a027
• 作为产物：
  描述：

  N-(4-氯-2-硝基苯基)乙酰胺 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-氯苯并呋喃
  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

• Ammonium Sulphate—Magnesium Promoted Selective Reduction of Aromatic Nitro Compounds
  作者：Dipak Prajapati、Harsha N. Borah、Jagir S. Sandhu、Anil C. Ghosh

  DOI：10.1080/00397919508011478

  日期：1995.12

  Abstract Various nitroarenes and 2,1,3-benznooxadiazole-1-oxides were selectively and rapidly reduces to their corresponding amino and diamino compounds respectively in high yields using (NH4SO4-Mg/A1/Bi, a new reduction system.

  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。
• Quinoxaline derivatives
  申请人：Research Corporation

  公开号：US04343942A1

  公开（公告）日：1982-08-10

  The synthesis of quinoxaline and benzimidazole-N-oxides and of ester and amide derivatives of 3-hydroxy-2-quinoxalinecarboxylic acid by a novel process consisting of the reaction between a benzofuroxan and an activated methylene-containing compound under basic conditions.

  喹啉和苯并咪唑-N-氧化物的合成，以及3-羟基-2-喹啉羧酸的酯和酰胺衍生物的合成，通过一种新颖的过程实现，该过程包括在碱性条件下对苯并呋喃酰胺和含活性亚甲基的化合物进行反应。
• Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds
  作者：Jinyu Sheng、Ru He、Jie Xue、Chao Wu、Juan Qiao、Chao Chen

  DOI：10.1021/acs.orglett.8b01748

  日期：2018.8.3

  The Cu-catalyzed regioselective synthesis of phenazine N-oxides was realized from benzoxadiazoles and diaryliodonium salts. The process was initiated by the electrophilic arylation of benzoxadiazoles with diaryliodonium salts and followed by benzocyclization reactions. The further reduction of N-oxides in situ to phenazine scaffolds and deviation to organic fluorescent materials were readily accomplished

  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。
• 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。
• Discovery of 1,2,3-triazole based quinoxaline-1,4-di-N-oxide derivatives as potential anti-tubercular agents
  作者：Singireddi Srinivasarao、Adinarayana Nandikolla、Amaroju Suresh、Augustynowicz-Kopec Ewa、Agnieszka Głogowska、Balaram Ghosh、Banoth Karan Kumar、Sankaranarayanan Murugesan、Sravani Pulya、Himanshu Aggarwal、Kondapalli Venkata Gowri Chandra Sekhar

  DOI：10.1016/j.bioorg.2020.103955

  日期：2020.7

  A series of thirty one novel 2-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-3-methylquinoxaline-1,4-dioxide (7a-l), 3-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-6-chloro-2-methylquinoxaline-1,4-dioxide (8a-l) and 2-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-6,7-dichloro-3-methylquinoxaline-1,4-dioxide (9a-g) analogues were synthesized

  一系列三十一个新颖的2-（（（（1-（取代苯基）-1 H -1,2,3-三唑-4-基）甲氧基）羰基）-3-甲基喹喔啉-1,4-二氧化物（7a- l），3-（（（（（1-（取代苯基）-1 H -1,2,3-三唑-4-基）甲氧基）羰基）-6-氯-2-甲基喹喔啉-1,4-二氧化物（8a -l）和2-（（（（（1-（取代的苯基）-1 H -1,2,3-三唑-4-基）甲氧基）羰基）羰基）-6,7-二氯-3-甲基喹喔啉-1,4-合成了二氧化（9a-g）类似物，使用多种分析技术进行了表征，并开发了化合物8 g和9f的单晶。评价合成的化合物的体外抗结核活性结核分枝杆菌H37Rv菌株和两种临床分离株 210和规格 192.标题化合物的最小抑菌浓度（MIC）为30.35至252.00 µM。在测试的化合物中，8e，8l，9c和9d表现出中等活性（MIC = 47.6 – 52.0 µM），8a表现出显着的抗结核活性（MIC

表征谱图