2,1,3-苯噁二唑-5-甲醛 1-氧化物 | 19164-42-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 中文名称: 2,1,3-苯噁二唑-5-甲醛 1-氧化物
• 中文别名: 2,1,3-苯噁二唑-5-甲醛1-氧化物
• 英文名称: 5-formylbenzofuroxan
• 英文别名: 2,1,3-Benzoxadiazole-5-carbaldehyde 1-oxide；1-oxido-2,1,3-benzoxadiazol-1-ium-5-carbaldehyde
• CAS: 19164-42-2
• 化学式: C₇H₄N₂O₃
• mdl: MFCD00955927
• 分子量: 164.12
• InChiKey: XOGHVCWQRORUFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-氨基-3-硝基苯甲醛 生成 2,1,3-苯噁二唑-5-甲醛 1-氧化物
  参考文献：
  名称：

  潜在的抗白血病和免疫抑制药物。3.同环取代对4-硝基苯并2,1,3-恶二唑（4-硝基苯并呋喃）及其N-氧化物（4-硝基苯并呋喃）的体外药物活性的影响。

  摘要：

  DOI：

  10.1021/jm00273a012

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。
• [EN] OXAZOLIDINONE DERIVATIVES AS ANTIMICROBIALS<br/>[FR] DERIVES D'OXAZOLIDINONE A ACTIVITE ANTIMICROBIENNE
  申请人：RANBAXY LAB LTD

  公开号：WO2006035283A1

  公开（公告）日：2006-04-06

  The present invention relates to substituted phenyl oxazolidinones and processes for preparing thereof. This invention also relates to pharmaceutical compositions comprising compounds of the present invention. Such compounds can be useful antimicrobial agents that can be particularly effective against a number of human and veterinary pathogens, including gram-positive aerobic bacteria (e.g., multiple-resistant staphylococci, streptococci and enterococci), anaerobic organisms (e.g., Bacterioides spp. and Clostridia spp. species), and acid-fast organisms (e.g., Mycobacterium tuberculosis, Mycobacterium avium and Mycobacterium spp).Formula (I).

  本发明涉及取代苯基噁唑烷酮及其制备方法。本发明还涉及包含本发明化合物的药物组合物。这些化合物可以是有用的抗微生物剂，特别是对许多人类和兽医病原体具有特效，包括革兰氏阳性厌氧细菌（例如，多耐药葡萄球菌、链球菌和肠球菌）、厌氧菌（例如，拟杆菌属和梭菌属物种）和耐酸菌（例如，结核分枝杆菌、分枝杆菌和分枝杆菌属）。公式（I）。
• Discovery of phenoxybutanoic acid derivatives as potent endothelin antagonists with antihypertensive activity
  作者：Jin Cai、Ligang Liu、Kwon Ho Hong、Peng Wang、Lushen Li、Meng Cao、Chunlong Sun、Xiaoqing Wu、Xi Zong、Junqing Chen、Min Ji

  DOI：10.1016/j.bmc.2015.01.003

  日期：2015.2

  A series of phenoxybutanoic acid derivatives were synthesized and tested for their antagonistic activity on the contraction of the rat thoracic aortic ring induced by endothelin-1. Preliminary screening results showed that 6e and 6g with benzoheterocycles demonstrated significant antagonistic activities when compared to the reference compound BQ123. The results from additional assays for the binding affinity and selectivity for endothelin receptors showed that 6e was a selective ETA antagonist with a nanomolar IC50. Moreover, 6e was effective in relieving hypoxia-induced pulmonary arterial hypertension and right ventricular weight ratio. Therefore, 6e may have potential for further development as a therapeutic agent for the treatment of cardiovascular diseases. (c) 2015 Elsevier Ltd. All rights reserved.
• Ligand-based design, synthesis, and experimental evaluation of novel benzofuroxan derivatives as anti-Trypanosoma cruzi agents
  作者：Salomão Dória Jorge、Fanny Palace-Berl、Kerly Fernanda Mesquita Pasqualoto、Marina Ishii、Adilson Kleber Ferreira、Carolina Maria Berra、Rosemary Viola Bosch、Durvanei Augusto Maria、Leoberto Costa Tavares

  DOI：10.1016/j.ejmech.2013.03.053

  日期：2013.6

  A set of substituted-[N'-(benzofuroxan-5-yl)methylene]benzohydrazides (4a-t), previously designed and synthesized, was experimentally assayed against Trypanosoma cruzi, the etiological agent of Chagas' disease, one of the most neglected tropical diseases. Exploratory data analysis, Hansch approach and VolSurf formalism were applied to aid the ligand-based design of novel anti-T cruzi agents. The best 2D-QSAR model showed suitable statistical measures [n = 18; s = 0.11; F = 42.19; R-2 = 0.90 and Q(2) = 0.77 (SDEP = 0.15)], and according to the optimum 3D-QSAR model [R-2 = 0.98, Q(2) = 0.93 (SDEP = 0.08)], three latent variables explained 62% of the total variance from original data. Steric and hydrophobic properties were pointed out as the key for biological activity. Based upon the findings, six novel benzofuroxan derivatives (4u-z) were designed, synthesized, and in vitro assayed to perform the QSAR external prediction. Then, the predictability for the both models, 2D-QSAR (R-pred(2) = 0.91) and 3D-QSAR (R-pred(2) = 0.77), was experimentally validated, and compound 4u was identified as the most active anti-T. cruzi hit (IC50 = 3.04 mu M). (C) 2013 Elsevier Masson SAS. All rights reserved.
• Second generation of 5-ethenylbenzofuroxan derivatives as inhibitors of Trypanosoma cruzi growth: Synthesis, biological evaluation, and structure–activity relationships
  作者：Williams Porcal、Paola Hernández、Gabriela Aguirre、Lucía Boiani、Mariana Boiani、Alicia Merlino、Ana Ferreira、Rossanna Di Maio、Ana Castro、Mercedes González、Hugo Cerecetto

  DOI：10.1016/j.bmc.2007.01.009

  日期：2007.4

  In vitro growth inhibitory activity of 21 new 5-ethenylbenzofuroxan derivatives against the protozoan parasite Trypanosoma cruzi, the causative agent of American trypanosomiasis, was studied. The designed compounds possess the previously described exigencies for optimal anti-parasite activity, the 5-ethenylbenzofuroxanyl moiety with different substituents. The synthetic key for preparing the derivatives was the Wittig procedure, that when 5-formylbenzofuroxan was used as the electrophile the corresponding deoxygenated products were marginally generated. Four of the new derivatives displayed remarkable in vitro activities against the epimastigote form of three strains of T cruzi, Tulahuen 2, CL Brener, and Y. While the three deoxygenated analogues biologically assayed resulted inactives. Unspecific cytotoxicity was evaluated using human macrophages and active derivatives were not toxic at a concentration at least 13 times that Of its IC50 against T cruzi (CL Brener strain). From the preliminary structure-activity relationship studies lipophilicity and electronic requirements were found relevant to anti-T cruzi activity. Active compounds are more lipophilic than inactive ones and it was also identified that an optimum value of R Swain-Lupton's descriptor is required for optimal activity. (c) 2007 Elsevier Ltd. All rights reserved.