5-benzofuroxanaldehyde oxime | 241818-88-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 5-benzofuroxanaldehyde oxime
• 英文别名: 5-hydroxyiminomethylbenzofuroxan；N-[(1-oxido-2,1,3-benzoxadiazol-1-ium-5-yl)methylidene]hydroxylamine
• CAS: 241818-88-2
• 化学式: C₇H₅N₃O₃
• 分子量: 179.135
• InChiKey: OCRVAHGMCUFQFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-benzofuroxanaldehyde oxime 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以90%的产率得到5-benzofuroxancarbonitrile
  参考文献：
  名称：

  摘要：

  Purpose. To investigate the effect of benzofusion on NO donor properties and related biological activities of the furoxan system. The biological properties considered were the ability to increase the cytosolic levels of cCMP in C6 cells and vasodilation.Methods. NO donor properties were investigated either in the presence or the absence of cysteine by using the Griess reaction, chemiluminescence, and gas chromatography. Increase of cytosolic cGMP levels were evaluated by radioimmunoassay. Vasodilating activity was assessed on rat aorta strips precontracted with noradrenaline, in the presence and the absence of oxyhemoglobin (HbO(2)) and methylene blue (MB), respectively.Results. Benzofuroxan and its methyl and cyano derivatives were unable to release NO under the experimental conditions. Generally these compounds displayed feeble vasodilating properties and were able to weakly stimulate soluble guanylate cyclase (sGC). By contrast, benzodifuroxan and benzotrifuroxan were able to produce both NO. and its reduced form NO-, the nitroxyl anion. They displayed potent vasodilating properties and were able to increase cytosolic levels of cGMP in a concentration-dependent manner.Conclusions. The simple benzofuroxans considered here are devoid of the capability to release NO, they weakly stimulate sGC as well as manifest feeble vasodilating properties by a mechanism that does not involve a thiol-induced NO production. By contrast, benzodifuroxan and benzotrifuroxan behave as typical NO donor furoxans.

  DOI：

  10.1023/a:1018974409622
• 作为产物：
  描述：

  2,1,3-苯噁二唑-5-甲醛 1-氧化物 在 盐酸羟胺 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 0.5h， 以95%的产率得到5-benzofuroxanaldehyde oxime
  参考文献：
  名称：

  摘要：

  Purpose. To investigate the effect of benzofusion on NO donor properties and related biological activities of the furoxan system. The biological properties considered were the ability to increase the cytosolic levels of cCMP in C6 cells and vasodilation.Methods. NO donor properties were investigated either in the presence or the absence of cysteine by using the Griess reaction, chemiluminescence, and gas chromatography. Increase of cytosolic cGMP levels were evaluated by radioimmunoassay. Vasodilating activity was assessed on rat aorta strips precontracted with noradrenaline, in the presence and the absence of oxyhemoglobin (HbO(2)) and methylene blue (MB), respectively.Results. Benzofuroxan and its methyl and cyano derivatives were unable to release NO under the experimental conditions. Generally these compounds displayed feeble vasodilating properties and were able to weakly stimulate soluble guanylate cyclase (sGC). By contrast, benzodifuroxan and benzotrifuroxan were able to produce both NO. and its reduced form NO-, the nitroxyl anion. They displayed potent vasodilating properties and were able to increase cytosolic levels of cGMP in a concentration-dependent manner.Conclusions. The simple benzofuroxans considered here are devoid of the capability to release NO, they weakly stimulate sGC as well as manifest feeble vasodilating properties by a mechanism that does not involve a thiol-induced NO production. By contrast, benzodifuroxan and benzotrifuroxan behave as typical NO donor furoxans.

  DOI：

  10.1023/a:1018974409622

文献信息

• 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。
• 2<i>H</i>-Benzimidazole 1,3-Dioxide Derivatives:  A New Family of Water-Soluble Anti-Trypanosomatid Agents
  作者：Mariana Boiani、Lucía Boiani、Ana Denicola、Susana Torres de Ortiz、Elva Serna、Ninfa Vera de Bilbao、Luis Sanabria、Gloria Yaluff、Héctor Nakayama、Antonieta Rojas de Arias、Celeste Vega、Miriam Rolan、Alicia Gómez-Barrio、Hugo Cerecetto、Mercedes González

  DOI：10.1021/jm0600343

  日期：2006.6.1

  Three series of benzimidazole N-oxide derivatives were developed and were examined for their activity against trypanosomatid parasites (Trypanosoma cruzi and Leishmania spp.). 2H-Benzimidazole 1,3-dioxides displayed remarkable in vitro activities against both parasites, with derivatives 28, 29, and 32 being the most potent (IC50 < 5 mu M) against the epimastigote form of T. cruzi and 28, 33, and 35 the most potent against the promastigote form of Leishmania spp. Unspecific cytotoxicity was evaluated using murine macrophages, and derivative 33 was not toxic at a concentration 30 times that of its IC50 against T. cruzi that was completely toxic for Leishmania spp., implying that the series of 2H-benzimidazole 1,3-dioxides is selective toward both trypanosomatid parasites. Derivatives 33 and 35 were submitted to an in vivo assay using an acute model of Chagas' disease and a short-term treatment (30 mg/kg/day orally administrated as aqueous solution, during 10 days). While in the control (untreated) and Benznidazole (50 mg/kg/day) groups survival fraction was 60.0% and 87.5%, respectively, none of the animals treated with derivatives 33 and 35 died. From the preliminary structure-activity relationship studies reduction potential and electrophilicity were found relevant to anti-T. cruzi activity. Active compounds are better electrophiles and more easily reduced than inactive ones.