5-(3-硝基苯基)-1,3,4-噁二唑-2-胺 | 7659-02-1

• 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-硝基苯基)-1,3,4-噁二唑-2-胺
• 英文名称: 2-amino-5-(3-nitrophenyl)-1,3,4-oxadiazole
• 英文别名: 5-(3-nitrophenyl)-1,3,4-oxadiazol-2-amine
• CAS: 7659-02-1
• 化学式: C₈H₆N₄O₃
• mdl: MFCD00469759
• 分子量: 206.161
• InChiKey: ZCDYCESVPSXZFM-UHFFFAOYSA-N

物化性质

• 溶解度：
  23.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 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：
  111
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(3-硝基苯基)-1,3,4-噁二唑-2-胺 在 盐酸 、 铜 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.33h， 生成 2-Chloro-5-(3-nitrophenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, antibacterial evaluation and QSAR studies of 7-[4-(5-aryl-1,3,4-oxadiazole-2-yl)piperazinyl] quinolone derivatives

  摘要：

  A series of 7-[4-(5-aryl-1,3,4-oxadiazole-2-yl)piperazinyl] quinolones (I-XXI) were synthesized using an appropriate synthetic route and characterized by elemental and spectral analysis. The antibacterial activities of all the synthesized compounds were evaluated against identifiable bacterial strains. Compounds III, IV, VII, VIII, IX, X, XI, XV, & XVIII showed better activity than parent compound against all the selected strains. QSAR study on the synthesized molecules tested for their antibacterial activity was performed using multiple linear regression method. Generated models revealed a decrease in HOMO energy as favorable descriptor for determining and predicting the antibacterial activity of the synthesized compounds. Further, the developed models were cross validated using LOO method for their predictive nature. (C) 2011 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.04.035
• 作为产物：
  描述：

  间硝基苯甲醛 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 生成 5-(3-硝基苯基)-1,3,4-噁二唑-2-胺
  参考文献：
  名称：

  芳基恶二唑连接的 1,2,4-三嗪衍生物作为抗惊厥药的设计、合成和药理学评价

  摘要：

  一系列新的棒状芳基恶二唑-1,2,4-三嗪衍生物(6a-l)使用适当的化学路线设计和合成。这些结构被设计成具有任何化合物所需的结构元素，以成为潜在的抗惊厥药。使用最大电休克发作 (MES)、皮下戊四唑诱发的癫痫发作 (scPTZ) 进行抗惊厥活性的初步筛选，并通过运动损伤测试和光度计测试评估行为活动。衍生物 6-((5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)amino)-1,2,4-triazine-3(2H)-thione (6f)和 6-( (5-(4-羟基苯基)-1,3,4-恶二唑-2-基)氨基)-1,2,4-三嗪-3(2H)-硫酮(6g)揭示了对 MES 和 scPTZ 的显着活性，表明这些化合物对全身强直-阵挛和失神发作均有效。对先导化合物(6g)进行了进一步的定量评估，并成为最有效的抗惊厥药，中位有效剂量为 28.5 mg/kg (MES

  DOI：

  10.1007/s00044-022-02880-4

文献信息

• Facile Method for the Conversion of Semicarbazones/Thiosemicarbazones into Azines (Under Microwave Irradiation) and Oxadiazoles (by Grinding)
  作者：Gautam Chattopadhyay、Partha Sinha Ray

  DOI：10.1080/00397911.2010.515334

  日期：2011.9.1

  Abstract In an effective transformation, semicarbazones/thiosemicarbazones are smoothly converted into azines under microwave irradition. Oxadiazoles are also obtained from semicarbazones by reaction with bromine generated in situ via a grinding reaction in the solid phase.

  摘要 在有效的转化过程中，缩氨基脲/缩氨基硫脲在微波照射下顺利转化为吖嗪。恶二唑也可通过与通过固相研磨反应原位产生的溴反应而从缩氨基脲反应获得。
• 一种含二茂铁基噁二唑基Mannich碱的制备 方法
  申请人：陕西科技大学

  公开号：CN107216357B

  公开（公告）日：2020-02-21

  本发明提供了一种含二茂铁基噁二唑基Mannich碱的制备方法。将A mol 2‑氨基‑5‑取代‑1,3,4‑噁二唑、B mol取代醛、E mol催化剂与溶剂无水乙醇加入到带有回流冷凝管的干燥三口烧瓶中，加入C mol乙酰基二茂铁的无水乙醇溶液，在室温下进行反应，反应时间为3～6h，其中A:B:C:E＝(0.7～1):(1～45):1:(1.1～1.5)，反应结束后，将反应混合液减压蒸馏蒸除溶剂，经柱色谱即得含二茂铁基噁二唑基Mannich碱。本发明操作简单，反应条件温和，设备要求低，产品纯度高，所用催化剂为硝酸铋，廉价易得。
• 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, In vitro α-Glucosidase Inhibitory Potential and Molecular Docking Studies of 2-Amino-1,3,4-Oxadiazole Derivatives
  作者：Hayat Ullah、Fazal Rahim、Muhammad Taha、Raffaqat Hussain、Abdul Wadood、Mohsan Nawaz、Zainul Wahab、Kanwal、Khalid M. Khan

  DOI：10.2174/1573406415666190612150447

  日期：2020.9.7

  In the recent past, we have synthesized and reported different derivatives of oxadiazoles as potential α-glucosidase inhibitors, keeping in mind, the pharmacological aspects of oxadiazole moiety and in continuation of our ongoing research on the chemistry and bioactivity of new heterocyclic compounds.

  1,3,4-Oxadiazole derivatives (1-14) have been synthesized and characterized by different spectroscopic techniques such as 1H-, 13C-NMR and HREI-MS.

  The synthetic derivatives were screened for α-glucosidase inhibitory potential. All compounds exhibited good inhibitory activity with IC50 values ranging between 0.80 ± 0.1 to 45.1 ± 1.7 μM in comparison with the standard acarbose having IC50 value 38.45 ± 0.80 μM.

  Thirteen compounds 1-6 and 8-14 showed potential inhibitory activity as compared to the standard acarbose having IC50 value 38.45 ± 0.80 μM, however, only one compound 7 (IC50 = 45.1 ± 1.7 μM) was found to be less active. Compound 14 (IC50 = 0.80 ± 0.1 μM) showed promising inhibitory activity among all synthetic derivatives. Molecular docking studies were also conducted for the active compounds to understand the ligand-enzyme binding interactions.

  背景：最近，我们合成并报告了不同的氧代二唑衍生物作为潜在的α-葡萄糖苷酶抑制剂，考虑到氧代二唑基团的药理学方面，并延续我们对新异环化合物的化学和生物活性研究。 方法：合成和表征了1,3,4-氧代二唑衍生物（1-14），并通过不同的光谱技术如1H-、13C-NMR和HREI-MS进行了表征。 结果：合成的衍生物被筛选用于α-葡萄糖苷酶抑制潜力。所有化合物在抑制活性方面表现出良好的活性，IC50值在0.80±0.1至45.1±1.7μM之间，与标准药物阿卡波糖的IC50值38.45±0.80μM相比。 结论：化合物1-6和8-14中的十三种化合物显示出潜在的抑制活性，与具有IC50值38.45±0.80μM的标准药物阿卡波糖相比，然而，只有一种化合物7（IC50=45.1±1.7μM）显示出较低的活性。化合物14（IC50=0.80±0.1μM）在所有合成衍生物中表现出有希望的抑制活性。还进行了活性化合物的分子对接研究，以了解配体-酶结合相互作用。
• 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。