5-(3-溴苯基)-1,3,4-噁二唑-2-胺 | 109060-66-4

• 物质功能分类: 医药中间体 - 杂环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(3-溴苯基)-1,3,4-噁二唑-2-胺
• 英文名称: 5-(3-bromophenyl)-1,3,4-oxadiazol-2-amine
• CAS: 109060-66-4
• 化学式: C₈H₆BrN₃O
• mdl: MFCD04627325
• 分子量: 240.059
• InChiKey: CVVNMXRTDJRCHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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：
  64.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P301+P310
• 危险品运输编号：
  2811
• 危险性描述：
  H301

反应信息

• 作为反应物：
  描述：

  5-(3-溴苯基)-1,3,4-噁二唑-2-胺 生成 2-(4-bromo-phenyl)-5-oxo-5H-[1,3,4]oxadiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  Gehlen,H.; Simon,B., Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1970, vol. 303, p. 501 - 510

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴苯甲酰氯 在 1,3-二溴-5,5-二甲基海因 、 potassium iodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 异丙醇 、 乙腈 为溶剂， 反应 25.0h， 生成 5-(3-溴苯基)-1,3,4-噁二唑-2-胺
  参考文献：
  名称：

  Discovery and Biophysical Characterization of 2-Amino-oxadiazoles as Novel Antagonists of PqsR, an Important Regulator of Pseudomonas aeruginosa Virulence

  摘要：

  The human pathogen Pseudomonas aeruginosa employs alkyl quinolones for cell-to-cell communication. The Pseudomonas quinolone signal (PQS) regulates various virulence factors via interaction with the transcriptional regulator PqsR. Therefore, we consider the development of PqsR antagonists a novel strategy to limit the pathogenicity of P. aeruginosa. A fragment identification approach using surface plasmon resonance screening led to the discovery of chemically diverse PqsR ligands. The optimization of the most promising hit (5) resulted in the oxadiazole-2-amine 37 showing pure antagonistic activity in Escherichia coli (EC50 = 7.5 mu M) and P. aeruginosa (EC50 = 38.5 mu M) reporter gene assays. 37 was able to diminish the production of the PQS precursor HHQ in a PqsH-deficient P. aeruginosa mutant The level of the major virulence factor pyocyanin was significantly reduced in wild-type P. aeruginosa. In addition, site-directed mutagenesis in combination with isothermal titration calorimetry and NMR INPHARMA experiments revealed that the identified ligands bind to the same site of PqsR by adopting different binding modes. These findings will be utilized in a future fragment growing approach aiming at novel therapeutic options for the treatment of P. aeruginosa infections.

  DOI：

  10.1021/jm400830r

文献信息

• Bioactive amide and α-aminophosphonate inhibitors for methicillin-resistant Staphylococcus aureus (MRSA)
  作者：Nader M. Boshta、Enas A. Elgamal、Ibrahim E. T. El-Sayed

  DOI：10.1007/s00706-018-2303-y

  日期：2018.12

  structure–activity relationships of new derivatives of 2-acylamino-1,3,4-oxadiazole were explored with focus on the substitution of the aromatic rings. The in vitro antibacterial activity of these compounds against MRSA strain was evaluated using agar disc diffusion method. These inhibitors have an amide linker between 1,3,4-oxadiazole ring and the aromatic ring B. The role of this linker on the bioactivity of the

  摘要最近已经开发了2-酰基氨基-1,3,4-恶二唑的支架作为针对MRSA的转糖基化酶抑制剂。在本研究中，研究了2-酰基氨基-1,3,4-恶二唑新衍生物的结构-活性关系，重点是芳香环的取代。使用琼脂圆盘扩散法评估了这些化合物对MRSA菌株的体外抗菌活性。这些抑制剂在1,3,4-恶二唑环和芳环B之间具有酰胺连接基。还研究了该连接基对化合物生物活性的作用。结果表明，有希望的2- α系列-氨基膦酸酯-1,3,4-恶二唑作为MRSA菌株的抑制剂。这两个系列都揭示了两个结构特征，这些结构特征似乎是抗MRSA活性必不可少的，第一个是在芳香环B的间位和对位引入两个吸电子基团，从而提高了抗MRSA菌株的活性。第二个是新的α-氨基膦酸酯连接基，它是相应酰胺连接基的生物立体异构体，并与酰胺衍生物具有可比的结果。 图形概要
• Synthesis, telomerase inhibitory and anticancer activity of new 2-phenyl-4H-chromone derivatives containing 1,3,4-oxadiazole moiety
  作者：Xu Han、Yun Long Yu、Duo Ma、Zhao Yan Zhang、Xin Hua Liu

  DOI：10.1080/14756366.2020.1864630

  日期：2021.1.1

  66 2-phenyl-4H-chromone derivatives containing amide and 1,3,4-oxadiazole moieties were prepared as potential telomerase inhibitors. The results showed most of the title compounds exhibited significantly inhibitory activity on telomerase. Among them, some compounds demonstrated the most potent telomerase inhibitory activity (IC50 < 1 µM), which was significantly superior to the staurosporine (IC50

  摘要 根据先前的研究，制备了 66 种含有酰胺和 1,3,4-恶二唑部分的 2-苯基-4H-色酮衍生物作为潜在的端粒酶抑制剂。结果显示大多数标题化合物对端粒酶表现出显着的抑制活性。其中，一些化合物表现出最有效的端粒酶抑制活性（IC 50 < 1 µM），明显优于星形孢菌素（IC 50 = 6.41 µM）。此外，总结了清晰的构效关系，表明甲氧基的取代以及苯环上取代基的位置、类型和数量对端粒酶活性有显着影响。其中，化合物A33对端粒酶有显着的抑制作用。流式细胞仪分析表明，化合物A33可以将MGC-803细胞周期阻滞在G2/M期，并以浓度依赖性方式诱导细胞凋亡。同时，Western blotting 显示该化合物可以降低作为端粒酶片段的dyskerin 的表达。
• Synthesis and amelioration of inflammatory paw edema by novel benzophenone appended oxadiazole derivatives by exhibiting cyclooxygenase-2 antagonist activity
  作者：Naveen Puttaswamy、Vikas H. Malojiao、Yasser Hussein Eissa Mohammed、Ankith Sherapura、B.T. Prabhakar、Shaukath Ara Khanum

  DOI：10.1016/j.biopha.2018.04.167

  日期：2018.7

  Ten new 2(4-hydroxy-3-benzoyl) benzamide-5-phenyl-1,3,4-oxadiazole derivatives () were synthesized by coupling 3-benzoyl-4-hydroxybenzoic acid ( with 2-amino-5-phenyl-1,3,4-oxadiazoles (). The structures of these compounds were confirmed by IR, H, C NMR, and mass spectra, and also by elemental analyses. The anti-inflammatory activity of the compounds were investigated by screening them against human

  通过将3-苯甲酰基-4-羟基苯甲酸（5）与2-氨基偶联，合成了十个新的2（4-羟基-3-苯甲酰基）苯甲酰胺-5-苯基-1,3,4-恶二唑衍生物（10a-j）。 -5-苯基-1,3,4-恶二唑（9a-j）。这些化合物的结构通过IR，1 H，13 C NMR和质谱以及元素分析确认。通过体外筛选化合物对抗人红细胞（HRBC）来研究化合物10a-j的抗炎活性。结果表明，在该系列中，具有羟基取代基的化合物10j，特别是在与恶二唑环的第5个碳原子连接的苯环的邻位上，与对照相比具有显着的膜稳定活性。进一步，进行了体内鸡绒膜尿囊膜（CAM）和大鼠角膜抗血管生成测定，以评估化合物10j对内皮细胞迁移的影响。这证实了化合物10j抑制内皮细胞的增殖。抗炎研究发现了角叉菜胶诱发的大鼠后爪水肿的改善。进一步的体内和计算机模拟方法揭示了炎症标记酶环氧合酶2（Cox-2）和髓过氧化物酶（MPO）的抑制作用。研究报告说，
• Microwave Assisted Synthesis and Spectral Analysis of Schiff Bases Derived from 2-Amino-5-Aryl-1,3,4-Oxadiazoles
  作者：SANJEEV KUMAR、SNEHA YADAV、SUDHA JADON、VIPIN KUMAR、ABDALLA M. KHEDR、KISHAN C. GUPTA

  DOI：10.13005/ojc/280438

  日期：2012.12.22

  Microwave assisted synthesis of new Schiff bases derived from 2-amino-5-substituted aryl- 1,3,4-oxadiazoles with substituted aromatic aldehyde have been carried out. The chemical structures of the prepared Schiff bases have been investigated by analytical and spectral methods.

  微波辅助合成了由2-氨基-5-取代的芳基-1,3,4-恶二唑与取代的芳族醛衍生的新席夫碱。制备的席夫碱的化学结构已通过分析和光谱方法进行了研究。
• A Facile Microwave Assisted Synthesis and Spectral Analysis of 2-Amino-5-substituted phenyl-1,3,4-Oxadiazoles
  作者：SANJEEV KUMAR、SNEHA YADAV、SUDHA JADON、VIPIN KUMAR、ABDALLA M. KHEDR、KISHAN C. GUPTA GUPTA

  DOI：10.13005/ojc/280441

  日期：2012.12.22

  An efficient synthesis for the preparation of some 2-amino-5-substituted phenyl-1,3,4oxadiazoles by using both conventional and microwave method have been devised. The obtained results revealed that, microwave assisted technique is efficient, eco-friendly and inexpensive method which not only give higher yield but also reduces the reaction time significantly. The resulting compounds were characterized

  已经设计了一种有效的合成方法，该方法通过使用常规方法和微波方法制备一些2-氨基-5-取代的苯基-1,3,4-恶二唑。所得结果表明，微波辅助技术是一种高效，环保，廉价的方法，不仅产率较高，而且反应时间明显缩短。通过IR，1 H-NMR，UV-Vis和质谱分析对所得化合物进行表征。