(1-氧代-2,1,3-苯并恶二唑-5-基)甲醇 | 175609-23-1

• 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: (1-氧代-2,1,3-苯并恶二唑-5-基)甲醇
• 中文别名: 2-苯基吗啉
• 英文名称: 5-(hydroxymethyl)benzo<1,2-c>1,2,5-oxadiazole N₁-oxide
• 英文别名: 5-hydroxymethylbenzofuroxan；2,1,3-Benzoxadiazole-5-methanol, 1-oxide；(1-oxido-2,1,3-benzoxadiazol-1-ium-5-yl)methanol
• CAS: 175609-23-1
• 化学式: C₇H₆N₂O₃
• 分子量: 166.136
• InChiKey: PGGQDQFDAHJMTE-UHFFFAOYSA-N

物化性质

• 沸点：
  357.6±34.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1-氧代-2,1,3-苯并恶二唑-5-基)甲醇 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以92%的产率得到2,1,3-苯噁二唑-5-甲醛 1-氧化物
  参考文献：
  名称：

  Benzofurazanyl- and benzofuroxanyl-1,4-dihydropyridines: synthesis, structure and calcium entry blocker activity

  摘要：

  The synthesis, structural characterization and calcium blocking activity of a series of benzofurazanyl-1,4-dihydropyridines (18 and 19) and benzofuroxanyl analogues (20 and 21) are reported. H-1-NMR showed that all the benzofuroxan derivatives exist in solution as tautomeric mixtures. The predominant tautomeric form in solution of the derivative 20 (dimethyl 1,4-dihydro-2,6-dimethyl-4-(4-benzofuroxanyl)-3,5-pyridinedicarboxylate) is also the one preferred in the solid state as shown by X-ray analysis. The conformation in the solid state of the benzofurazanyl analogue is also reported. Calcium entry blocker activity of the dihydropyridine derivatives 18-21 has been evaluated in isolated rabbit basilar artery as relaxation of calcium-induced contractions in high K+-depolarizing solution. All the compounds displayed high potency. The activity of benzofurazan derivatives was not changed by the N-oxidation. The two most active compounds 18 and 20 were as potent as Nifedipine.

  DOI：

  10.1016/s0223-5234(96)80001-8
• 作为产物：
  描述：

  5-甲基苯并呋喃-1-氧化物 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 水 、 calcium carbonate 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 反应 7.0h， 生成 (1-氧代-2,1,3-苯并恶二唑-5-基)甲醇
  参考文献：
  名称：

  Benzofurazanyl- and benzofuroxanyl-1,4-dihydropyridines: synthesis, structure and calcium entry blocker activity

  摘要：

  The synthesis, structural characterization and calcium blocking activity of a series of benzofurazanyl-1,4-dihydropyridines (18 and 19) and benzofuroxanyl analogues (20 and 21) are reported. H-1-NMR showed that all the benzofuroxan derivatives exist in solution as tautomeric mixtures. The predominant tautomeric form in solution of the derivative 20 (dimethyl 1,4-dihydro-2,6-dimethyl-4-(4-benzofuroxanyl)-3,5-pyridinedicarboxylate) is also the one preferred in the solid state as shown by X-ray analysis. The conformation in the solid state of the benzofurazanyl analogue is also reported. Calcium entry blocker activity of the dihydropyridine derivatives 18-21 has been evaluated in isolated rabbit basilar artery as relaxation of calcium-induced contractions in high K+-depolarizing solution. All the compounds displayed high potency. The activity of benzofurazan derivatives was not changed by the N-oxidation. The two most active compounds 18 and 20 were as potent as Nifedipine.

  DOI：

  10.1016/s0223-5234(96)80001-8

文献信息

• 1,2,5-Oxadiazole <i>N</i>-Oxide Derivatives and Related Compounds as Potential Antitrypanosomal Drugs:  Structure−Activity Relationships
  作者：Hugo Cerecetto、Rossanna Di Maio、Mercedes González、Mariela Risso、Patricia Saenz、Gustavo Seoane、Ana Denicola、Gonzalo Peluffo、Celia Quijano、Claudio Olea-Azar

  DOI：10.1021/jm9805790

  日期：1999.6.1

  The syntheses of a new series of derivatives of 1,2,5-oxadiazole N-oxide, benzo[1,2-c]1,2,5-oxadiazole N-oxide, and quinoxaline di-hr-oxide are described. In vitro antitrypanosomal activity of these compounds was tested against epimastigote forms of Trypanosoma cruzi. For the most effective drugs, derivatives IIIe and IIIf, the 50% inhibitory dose (ID50) was determined as well as their cytotoxicity against mammalian fibroblasts. Electrochemical studies and ESR spectroscopy show that the highest activities observed are associated with the facile mono-electronation of the N-oxide moiety. Lipophilic-hydrophilic balance of the compounds could also play an important role in their effectiveness as antichagasic drugs.
• <i>In Vivo</i> Anti-Chagas Vinylthio-, Vinylsulfinyl-, and Vinylsulfonylbenzofuroxan Derivatives
  作者：Williams Porcal、Paola Hernández、Mariana Boiani、Gabriela Aguirre、Lucía Boiani、Agustina Chidichimo、Juan J. Cazzulo、Nuria E. Campillo、Juan A. Paez、Ana Castro、R. Luise Krauth-Siegel、Carolina Davies、Miguel Ángel Basombrío、Mercedes González、Hugo Cerecetto

  DOI：10.1021/jm070604e

  日期：2007.11.1

  New benzofuroxans were developed and studied as antiproliferative Trypanosoma cruzi agents. Compounds displayed remarkable in vitro activities against different strains, Tulahuen 2, CL Brener and Y. Its unspecific cytotoxicity was evaluated using human macrophages being not toxic at a concentration at least 8 times, and until 250 times, that of its T. cruzi IC50. Some biochemical pathways were studied, namely parasite respiration, cysteinyl active site enzymes and reaction with glutathione, as target for the mechanism of action. Not only T cruzi respiration but also Cruzipain or trypanothione reductase were not affected, however the most active derivatives, the vinylsulfinyl- and vinylsulfonyl-containing benzofuroxans, react with glutathione in a redox pathway. Furthermore, the compounds showed good in vivo activities when they were studied in an acute murine model of Chagas' disease. The compounds were able to reduce the parasite loads of animals with fully established T cruzi infections.
• Benzo[1,2-c]1,2,5-oxadiazole N-oxide derivatives as potential antitrypanosomal drugs. Part 3: Substituents-clustering methodology in the search for new active compounds
  作者：Gabriela Aguirre、Lucía Boiani、Hugo Cerecetto、Rossanna Di Maio、Mercedes González、Williams Porcal、Ana Denicola、Matías Möller、Leonor Thomson、Verónica Tórtora

  DOI：10.1016/j.bmc.2005.05.020

  日期：2005.12

  The results of a study on the use of Hansch's series design, cluster methodology, for the generation of newbenzo[1,2-c] 1,2, 5-oxadiazole N-oxide derivatives as antitrypanosomal compounds are described. In vitro activity of these compounds was tested against Tulahuen 2 strain of Trypanosoma cruzi. Clearly, the Hansch methodology allowed identifying two cluster-substituents suitable for further structural modifications. The most effective drugs, derivatives 11, 18, and 21, with 50% inhibitory concentration (IC50) of the same order as that of the reference drug, represent an excellent structural point of chemical modifications for the design of future drugs. Preliminary results from the study of the mechanism of action of these benzofuroxans point to perturbation of the mitochondrial electron chain, inhibiting parasite respiration. (c) 2005 Elsevier Ltd. All rights reserved.
• Benzofurazanyl- and benzofuroxanyl-1,4-dihydropyridines: synthesis, structure and calcium entry blocker activity
  作者：AM Gasco、G Ermondi、R Fruttero、A Gasco

  DOI：10.1016/s0223-5234(96)80001-8

  日期：1996.1

  The synthesis, structural characterization and calcium blocking activity of a series of benzofurazanyl-1,4-dihydropyridines (18 and 19) and benzofuroxanyl analogues (20 and 21) are reported. H-1-NMR showed that all the benzofuroxan derivatives exist in solution as tautomeric mixtures. The predominant tautomeric form in solution of the derivative 20 (dimethyl 1,4-dihydro-2,6-dimethyl-4-(4-benzofuroxanyl)-3,5-pyridinedicarboxylate) is also the one preferred in the solid state as shown by X-ray analysis. The conformation in the solid state of the benzofurazanyl analogue is also reported. Calcium entry blocker activity of the dihydropyridine derivatives 18-21 has been evaluated in isolated rabbit basilar artery as relaxation of calcium-induced contractions in high K+-depolarizing solution. All the compounds displayed high potency. The activity of benzofurazan derivatives was not changed by the N-oxidation. The two most active compounds 18 and 20 were as potent as Nifedipine.