3-(benzyloxy)benzoic acid 2-(2-cyanoethyl)hydrazide | 443296-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(benzyloxy)benzoic acid 2-(2-cyanoethyl)hydrazide
• 英文别名: 3-(benzyloxy)-N-(2-cyanoethyl)benzohydrazide；N'-(2-cyanoethyl)-3-phenylmethoxybenzohydrazide
• CAS: 443296-90-0
• 化学式: C₁₇H₁₇N₃O₂
• 分子量: 295.341
• InChiKey: IVHIRKOPYCFNKX-UHFFFAOYSA-N

物化性质

• 沸点：
  487.9±45.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯乙酰氯 、 3-(benzyloxy)benzoic acid 2-(2-cyanoethyl)hydrazide 在 potassium carbonate 作用下， 以 氯仿 、 乙醇 为溶剂， 反应 3.0h， 以63%的产率得到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
• 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 、 丙酮 为溶剂， 反应 79.0h， 生成 3-(benzyloxy)benzoic acid 2-(2-cyanoethyl)hydrazide
  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

• .BETA.-N-Cyanoethyl Acyl Hydrazide Derivatives: A New Class of .BETA.-Glucuronidase Inhibitors.
  作者：Khalid Mohammed Khan、Shahida Shujaat、Shagufta Rahat、Safdar Hayat、Atta-ur-Rahman、Muhammad Iqbal Choudhary

  DOI：10.1248/cpb.50.1443

  日期：——

  Eight new β-N-substituted acyl hydrazides along with their corresponding acyl derivatives were synthesized and screened for in vitro β-glucuronidase inhibition and found to be active against the enzyme. All of these compounds were found to be noncompetitive inhibitors except for N′-(2-cyanoethyl)-4-hydroxy benzohydrazide (10), which was found to be an uncompetitive inhibitor. Structure–activity relationship studies indicated that the benzyloxy group present in compounds 12 and 13 is responsible for the β-glucuronidase inhibition activity.

  合成了八种新的β-N-取代酰肼及其相应的酰基衍生物，并对它们进行了体外β-葡萄糖苷酶抑制活性筛选，发现它们对酶具有活性。除了N'-(2-氰乙基)-4-羟基苯甲酼肼（10）被发现是非竞争性抑制剂外，所有这些化合物都被发现是非竞争性抑制剂。结构-活性关系研究表明，化合物12和13中的苄氧基是导致β-葡萄糖苷酶抑制活性的原因。
• 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.