3-(4-Nitro-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid hydrazide | 259151-03-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-Nitro-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid hydrazide
• 英文别名: 3-(4-Nitrophenyl)-1,2,4-oxadiazole-5-carbohydrazide
• CAS: 259151-03-6
• 化学式: C₉H₇N₅O₄
• 分子量: 249.186
• InChiKey: XEBBRCUVLUTSGR-UHFFFAOYSA-N

物化性质

• 密度：
  1.525±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  肉桂醛 、 3-(4-Nitro-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid hydrazide 在 cerium(III) chloride heptahydrate 作用下， 以 乙醇 为溶剂， 以91%的产率得到3-(4-nitrophenyl)-N'-[(1E,2E)-3-phenylprop-2-en-1-ylidene]-1,2,4-oxadiazol-5-carbohydrazide
  参考文献：
  名称：

  N-酰基hydr和1,2,4-恶二唑的缀合导致活性抗疟药的鉴定

  摘要：

  由几种疟原虫引起的疟疾是全球范围内威胁生命的主要寄生虫感染。由于寄生虫对喹啉类药物有抗药性，因此有必要寻找抗疟药。在这里，我们报告两个新的1,2,4-恶二唑系列与N-酰基azo偶合物的结构设计，合成和抗寄生虫评价，两个组均被认为是特权结构，以及对16个抗疟活性的研究。描述的类似物。与未取代的衍生物相比，通过改变连接在苯环上的取代基，可以保留，增强或增加抗寄生虫活性。N中连接的二茂铁基和肉桂基部分取代取代的芳基环-酰基hydr消除了抗寄生虫反应，证明了与活性有关的结构特征。活性化合物显示出与甲氟喹相似的体外效价，但并非全部抑制β-血红素的形成。此外，活性化合物在HepG2细胞中显示出低细胞毒性，并且在未感染的红细胞中不会引起溶血。与氯喹相比，在伯氏疟原虫感染的小鼠中，该化合物减少了寄生虫血症，但在增加小鼠存活率方面显示出有限的功效，这表明仍需要药理学方面的改进。

  DOI：

  10.1016/j.bmc.2016.09.013
• 作为产物：
  描述：

  对硝基苯甲腈 在 盐酸羟胺 、 一水合肼 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 3-(4-Nitro-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid hydrazide
  参考文献：
  名称：

  Ferrocenylethenyl-substituted oxadiazoles with phenolic and nitro anchors as sensitizers in dye sensitized solar cells

  摘要：

  使用含酚和硝基锚定基团的二氧化三唑取代了二茂铁乙烯基，用作染料敏化太阳能电池（DSSCs）的敏化剂。

  DOI：

  10.1039/c8nj06242k

文献信息

• SYNTHESIS, BIOLOGICAL EVALUATION, AND STRUCTURAL STUDIES OF 3-PHENYL[ 1,2,4]OXADIAZOLE-5-CARBOXYLIC ACID BENZO[1,3]DIOXOL 5-YLMETHYLENE-HYDRAZIDE
  作者：J. M. Santos-Filho、J. G. de Lima、L. F. C. C. Leite、Ε. A. Ximenes、J. Β. P. da Silva、P. C. Lima、l. R. Pitta

  DOI：10.1515/hc.2005.11.1.29

  日期：2005.1

  A series of 1,2,4-oxadiazole combined with carbohydrazides residues, designed as possible bioactive compounds, was obtained in an attempt to analyse the effects of this molecular hybridization on the biological properties of the resulting compounds. They were tested for their antimicrobial and antimalarial activity. Ab initio calculations were performed in order to strengthen experimental NMR structural

  获得了一系列与碳酰肼残基结合的 1,2,4-恶二唑，被设计为可能的生物活性化合物，试图分析这种分子杂交对所得化合物的生物学特性的影响。对它们的抗微生物和抗疟活性进行了测试。进行了从头算计算以加强实验核磁共振结构数据。
• Optimization of anti-Trypanosoma cruzi oxadiazoles leads to identification of compounds with efficacy in infected mice
  作者：José Maurício dos Santos Filho、Diogo Rodrigo M. Moreira、Carlos Alberto de Simone、Rafaela Salgado Ferreira、James H. McKerrow、Cássio Santana Meira、Elisalva Teixeira Guimarães、Milena Botelho Pereira Soares

  DOI：10.1016/j.bmc.2012.08.047

  日期：2012.11

  oxadiazoles have anti-Trypanosoma cruzi activity at micromolar concentrations. These compounds are easy to synthesize and show a number of clear and interpretable structure–activity relationships (SAR), features that make them attractive to pursue potency enhancement. We present here the structural design, synthesis, and anti-T. cruzi evaluation of new oxadiazoles denoted 5a–h and 6a–h. The design of these

  我们最近表明，恶二唑在微摩尔浓度下具有抗克氏锥虫活性。这些化合物易于合成，并显示出许多清晰易懂的结构-活性关系（SAR），这些特征使它们对于增强效能具有吸引力。我们在此介绍新恶二唑类化合物的结构设计，合成和抗T. cruzi评估，表示为5a – h和6a – h。这些化合物的设计是基于恶二唑在T. cruzi蛋白酶cruzain上的计算对接的先前模型。我们测试了这些化合物抑制Cruzain催化活性的能力，但是我们发现酶的抑制作用与这些化合物的抗寄生虫活性之间没有相关性。但是，当我们针对整个寄生虫测试这些化合物时，我们发现了可靠的SAR数据。尽管这些恶二唑均未显示对哺乳动物细胞有毒性，但恶二唑6c（氟），6d（氯）和6e（溴）减少了副鞭毛的增殖，并对克鲁维耶氏酵母Y菌株的拟鞭毛象具有杀灭作用。恶二唑6c和6d的IC 50锥虫为9.5±2.8和3.5±1.8μM，而苯甲硝唑（目前用于南美锥虫病治疗的药物）的IC
• Synthesis, characterization, and anti-inflammatory evaluation of 1,2,4-oxadiazoles combined with thiosemicarbazide and 1,3,4-oxadiazole moieties
  作者：José M. dos Santos Filho、José G. de Lima、Lúcia F. C. C. Leite

  DOI：10.1002/jhet.133

  日期：2009.7

  The reaction of 1,2,4-oxadiazole carbohydrazides with phenyl isothiocyanate led to an unexpected ring cyclisation of the thiosemicarbazide derivatives , giving compounds as side products. These two new series were preliminarily evaluated for their anti-inflammatory activity, using the carrageenin induced edema protocol. J. Heterocyclic Chem., (2009).

  1,2,4-恶二唑碳酰肼的反应 和 异硫氰酸苯酯导致硫代氨基脲衍生物的意外环环化，给出化合物 作为副产品。使用角叉菜胶诱导的浮肿方案初步评估了这两个新系列的抗炎活性。J.杂环化​​学，（2009）。
• Synthesis and analgesic profile of novel N-containing heterocycle derivatives: arylidene 3-phenyl-1,2,4-oxadiazole-5-carbohydrazide
  作者：Lúcia Fernanda C.C. Leite、Mozart N. Ramos、João Bosco P. da Silva、Ana L.P. Miranda、Carlos A.M. Fraga、Eliezer J. Barreiro

  DOI：10.1016/s0014-827x(99)00094-4

  日期：1999.11

  This paper describes recent results of a research program aimed at the synthesis and pharmacological evaluation of new heterocyclic N-acylhydrazone (NAH) compounds, belonging to the arylidene (3-phenyl)-1,2,4-oxadiazolyl-5-carboxyhydrazide (8a-p) series. These compounds were structurally planned by applying the molecular hybridization strategy on previously described arylidene 1-phenylpyrazole-4-carbohydrazide (5) derivatives, considered as lead-compounds, which present potent analgesic properties. The analgesic profile of the title compounds 8a-p, evaluated in the model of abdominal constrictions induced by acetic acid, showed that the 4-methoxybenzylidene derivatives 8c and 8k were the most active ones, exhibiting a relative analgesic activity comparable with that of dipyrone 1 used as standard. (C) 1999 Elsevier Science S.A. All rights reserved.
• Design, synthesis and cruzain docking of 3-(4-substituted-aryl)-1,2,4-oxadiazole-N-acylhydrazones as anti-Trypanosoma cruzi agents
  作者：José Mauricio dos Santos Filho、Ana Cristina Lima Leite、Boaz Galdino de Oliveira、Diogo Rodrigo Magalhães Moreira、Milena S. Lima、Milena Botelho Pereira Soares、Lucia Fernanda C.C. Leite

  DOI：10.1016/j.bmc.2009.07.068

  日期：2009.9

  Research in recent years has demonstrated that the Trypanosoma cruzi cysteine protease cruzain (TCC) is a valid chemotherapeutic target, since inhibitors of this protease affect the pathology appropriately. By exploring the N-acylhydrazones (NAH) as privileged structures usually present in antiparasitic agents, we investigated a library of 16 NAH bearing the 3-(4-substituted-aryl)-1,2,4-oxadiazole scaffold (NAH 3a-h, 4a-h). The in vitro bioactivity against epimastigote and trypomastigote forms of T. cruzi was evaluated, and some NAH under study exhibited antitrypanosomal activity at concentrations that are not toxic to mammalian cells. The series of compounds based on the 3-(4-substituted-aryl)-1,2,4-oxadiazole scaffold revealed the remarkable importance of each substituent at the phenyl's 4-position for the inhibitory activity. Non-nitrated compounds 3a and 4e were found to be as potent as the reference drug, Benznidazole. In addition, the molecular origin of the antitrypanosomal properties for these series was investigated using docking studies of the TCC structure. (C) 2009 Elsevier Ltd. All rights reserved.