2-[3-(benzyloxy)phenyl]-5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[3-(benzyloxy)phenyl]-5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitrile
• 英文别名: 3-[5-Oxo-2-(3-phenylmethoxyphenyl)-1,3,4-oxadiazin-4-yl]propanenitrile
• 化学式: C₁₉H₁₇N₃O₃
• 分子量: 335.362
• InChiKey: UCPRLYWOCMLDQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  74.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羟基苯甲酸乙酯 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 氯仿 、 丙酮 为溶剂， 反应 82.0h， 生成 2-[3-(benzyloxy)phenyl]-5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitrile
  参考文献：
  名称：

  Synthesis and Biological Screening of 2-Substituted 5,6-Dihydro-5-oxo- 4H-1,3,4-oxadiazine-4-propanenitriles and of Their Intermediates

  摘要：

  To evaluate the effect of substituents on biological activities of electron-rich N-containing heterocycles, the variably 2-substituted 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles 26-33 were synthesized and evaluated for antibacterial, antifungal, and enzyme-inhibition activities. The target compounds were obtained from alkyl 4- or 3-hydroxy benzoates 1 and 2, respectively, and from methyl indoleacetate 3. The phenolic OH group of benzoates I and 2 were substituted with p-toluenesulfonyl ( --> 4 and 5), benzoyl ( 6 and 7), and benzyl groups ( 8 and 9) and then converted to 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles. To establish structure-activity relationships (SAR), a pharmacological screening of the intervening intermediates was also conducted, which revealed that the intermediate hydrazide 11 possesses significant antimicrobial and MAO-A inhibiting properties and intermediates 12,24,28, and 29 appreciable antifungal activities. Compound 7 inhibits a-chymotrypsin.

  DOI：

  10.1002/1522-2675(200202)85:2<559::aid-hlca559>3.0.co;2-a

文献信息

• Synthesis and Biological Screening of 2-Substituted 5,6-Dihydro-5-oxo- 4H-1,3,4-oxadiazine-4-propanenitriles and of Their Intermediates
  作者：Khalid Mohammed Khan、Shagufta Rahat、Muhammad Iqbal Choudhary、Atta-ur-Rahman、Usman Ghani、Shahnaz Perveen、Shagufta Khatoon、Ahsana Dar、Abdul Malik

  DOI：10.1002/1522-2675(200202)85:2<559::aid-hlca559>3.0.co;2-a

  日期：2002.2

  To evaluate the effect of substituents on biological activities of electron-rich N-containing heterocycles, the variably 2-substituted 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles 26-33 were synthesized and evaluated for antibacterial, antifungal, and enzyme-inhibition activities. The target compounds were obtained from alkyl 4- or 3-hydroxy benzoates 1 and 2, respectively, and from methyl indoleacetate 3. The phenolic OH group of benzoates I and 2 were substituted with p-toluenesulfonyl ( --> 4 and 5), benzoyl ( 6 and 7), and benzyl groups ( 8 and 9) and then converted to 5,6-dihydro-5-oxo-4H-1,3,4-oxadiazine-4-propanenitriles. To establish structure-activity relationships (SAR), a pharmacological screening of the intervening intermediates was also conducted, which revealed that the intermediate hydrazide 11 possesses significant antimicrobial and MAO-A inhibiting properties and intermediates 12,24,28, and 29 appreciable antifungal activities. Compound 7 inhibits a-chymotrypsin.