(2-hydroxyethyl)hydrazone of 4-(benzyloxy)benzaldehyde | 170300-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2-hydroxyethyl)hydrazone of 4-(benzyloxy)benzaldehyde
• 英文别名: 2-[2-[(4-Phenylmethoxyphenyl)methylidene]hydrazinyl]ethanol
• CAS: 170300-77-3
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: JEYPQOFRNPNYHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  53.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 (2-hydroxyethyl)hydrazone of 4-(benzyloxy)benzaldehyde 在 吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以38%的产率得到N-(2-hydroxyethyl)-N-[(4-phenylmethoxyphenyl)methylideneamino]acetamide
  参考文献：
  名称：

  Selective and potent monoamine oxidase type B inhibitors: substituted semicarbazones and acylhydrazones of aromatic aldehydes and ketones

  摘要：

  The synthesis and the evaluation of the monoamine oxidase A and B inhibitory activities of 21 new substituted acylhydrazones of various aromatic aldehydes and 4-(benzyloxy)acetophenone, and four substituted semicarbazones of benzaldehyde and 4-(benzyloxy)benzaldehyde, are described. The 4-(benzyloxy)phenyl group contributing to a high lipophilicity led to the most active compounds. One of these, compound 3g (IC50 = 3 nM, MAO A/MAO B selectivity > 33 000), was found to act as a reversible and probably tight-binding inhibitor. The studied acyclic hydrazones and semicarbazones are structurally related to other reversible and potent inhibitors, eg, heterocyclic compounds such as 1,3,4-oxadiazol-2(3H)-one derivatives in which the hydrazono group is intracyclic. Some of these new inhibitors might find use in the symptomatic treatment of neurodegenerative processes.

  DOI：

  10.1016/0223-5234(96)88258-4
• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 2-肼基乙醇 以 乙醇 为溶剂， 反应 1.0h， 以79%的产率得到(2-hydroxyethyl)hydrazone of 4-(benzyloxy)benzaldehyde
  参考文献：
  名称：

  Selective and potent monoamine oxidase type B inhibitors: substituted semicarbazones and acylhydrazones of aromatic aldehydes and ketones

  摘要：

  The synthesis and the evaluation of the monoamine oxidase A and B inhibitory activities of 21 new substituted acylhydrazones of various aromatic aldehydes and 4-(benzyloxy)acetophenone, and four substituted semicarbazones of benzaldehyde and 4-(benzyloxy)benzaldehyde, are described. The 4-(benzyloxy)phenyl group contributing to a high lipophilicity led to the most active compounds. One of these, compound 3g (IC50 = 3 nM, MAO A/MAO B selectivity > 33 000), was found to act as a reversible and probably tight-binding inhibitor. The studied acyclic hydrazones and semicarbazones are structurally related to other reversible and potent inhibitors, eg, heterocyclic compounds such as 1,3,4-oxadiazol-2(3H)-one derivatives in which the hydrazono group is intracyclic. Some of these new inhibitors might find use in the symptomatic treatment of neurodegenerative processes.

  DOI：

  10.1016/0223-5234(96)88258-4