5-(3-硝基苯基)-3-对甲苯基-1,2,4-恶二唑 | 352642-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-(3-硝基苯基)-3-对甲苯基-1,2,4-恶二唑
• 英文名称: 5-(3-nitrophenyl)-3-p-tolyl-1,2,4-oxadiazole
• 英文别名: Cambridge id 5802008；3-(4-methylphenyl)-5-(3-nitrophenyl)-1,2,4-oxadiazole
• CAS: 352642-88-7
• 化学式: C₁₅H₁₁N₃O₃
• 分子量: 281.271
• InChiKey: COLUDPXQBLWWFE-UHFFFAOYSA-N

物化性质

• 沸点：
  458.8±55.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  5

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  3-[3-(4-甲基苯基)-1,2,4-恶二唑-5-基]苯胺	3-[3-(4-Methylphenyl)-1,2,4-oxadiazol-5-YL]aniline	915921-22-1	C15H13N3O	251.288
  ——	2-(3,4-dimethoxyphenyl)-N-(3-(3-p-tolyl-1,2,4-oxadiazol-5-yl)phenyl)acetamide	1418206-37-7	C25H23N3O4	429.475

反应信息

• 作为反应物：
  描述：

  5-(3-硝基苯基)-3-对甲苯基-1,2,4-恶二唑 在 3-甲基吡啶 、 氯化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 2-(3,4-dimethoxyphenyl)-N-(3-(3-p-tolyl-1,2,4-oxadiazol-5-yl)phenyl)acetamide
  参考文献：
  名称：

  Design, Synthesis and Biological Activity Evaluation of 2,5-Diphenyl-1,3,4-oxadiazole Derivatives as Novel Inhibitors of Fructose-1,6-bisphosphatase

  摘要：

  Fructose-1,6-bisphosphatase (FBPase), an important gluconeogenic enzyme, catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate. The effort to discover new FBPase inhibitors was carried out by high-throughput screening (HTS) of a library of 56,000 lead-like compounds, and a 2,5-diphenyl-1,3,4-oxadiazole (3a, IC50 = 15.45 mu M) which bearing no phosphate group was identified as a potential FBPase inhibitor for the first time. Structure-activity-relationship (SAR) research of a series of analogues obtained by modifying the substituent groups and replacing the 1,3,4-oxadiazole with several other heterocycles disclosed the key structure and substituent groups related to the binding with FBPase.

  DOI：

  10.3987/com-12-12565
• 作为产物：
  描述：

  4-甲基苯甲酰胺肟 在 碳酸甲丙酯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 5-(3-硝基苯基)-3-对甲苯基-1,2,4-恶二唑
  参考文献：
  名称：

  Design, Synthesis and Biological Activity Evaluation of 2,5-Diphenyl-1,3,4-oxadiazole Derivatives as Novel Inhibitors of Fructose-1,6-bisphosphatase

  摘要：

  Fructose-1,6-bisphosphatase (FBPase), an important gluconeogenic enzyme, catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate. The effort to discover new FBPase inhibitors was carried out by high-throughput screening (HTS) of a library of 56,000 lead-like compounds, and a 2,5-diphenyl-1,3,4-oxadiazole (3a, IC50 = 15.45 mu M) which bearing no phosphate group was identified as a potential FBPase inhibitor for the first time. Structure-activity-relationship (SAR) research of a series of analogues obtained by modifying the substituent groups and replacing the 1,3,4-oxadiazole with several other heterocycles disclosed the key structure and substituent groups related to the binding with FBPase.

  DOI：

  10.3987/com-12-12565

文献信息

• A new method to synthesize 1,2,4-oxadiazoles by using DMTMM as condensing agent
  作者：Yijie Wang、Xu Cheng、Jing Xu、Lin Wang、Shouguo Zhang、Shuchen Liu、Tao Peng

  DOI：10.1016/j.tetlet.2023.154590

  日期：2023.7

  condensing agent for synthesis of 1,2,4-oxadiazoles from corresponding carboxylic acids and amidoximes in the mixed solvent of THF and NMP. First, carboxylic acids were activated by DMTMM, and then reacted with amidoximes to convert to O-acylated amidoximes. The unusual solvent system THF-NMP successfully promoted dehydration process of O-acylated amidoximes and 1,2,4-oxadiazoles were acquired in one-pot

  DMTMM作为缩合剂在THF和NMP的混合溶剂中由相应的羧酸和偕胺肟合成1,2,4-恶二唑。首先，DMTMM 活化羧酸，然后与偕胺肟反应，转化为 O-酰化偕胺肟。不寻常的溶剂体系 THF-NMP 成功地促进了 O-酰化偕胺肟的脱水过程，并在一锅法中获得了 1,2,4-恶二唑。该方法提供了一种方便快捷的 1,2,4-恶二唑合成方法，产率高。
• Design, Synthesis and Biological Activity Evaluation of 2,5-Diphenyl-1,3,4-oxadiazole Derivatives as Novel Inhibitors of Fructose-1,6-bisphosphatase
  作者：Fan Yang、Jia Li、Jing-Ya Li、Hai-Bing He、Yue-Yang Zhou、Ting Liu、Jie Tang、Xue-Ping Gong、Wen-Wei Qiu

  DOI：10.3987/com-12-12565

  日期：——

  Fructose-1,6-bisphosphatase (FBPase), an important gluconeogenic enzyme, catalyzes the hydrolysis of fructose 1,6-bisphosphate to fructose 6-phosphate. The effort to discover new FBPase inhibitors was carried out by high-throughput screening (HTS) of a library of 56,000 lead-like compounds, and a 2,5-diphenyl-1,3,4-oxadiazole (3a, IC50 = 15.45 mu M) which bearing no phosphate group was identified as a potential FBPase inhibitor for the first time. Structure-activity-relationship (SAR) research of a series of analogues obtained by modifying the substituent groups and replacing the 1,3,4-oxadiazole with several other heterocycles disclosed the key structure and substituent groups related to the binding with FBPase.