(2-cyanoethyl)hydrazone of 4-(benzyloxy)benzaldehyde | 170300-76-2

• 英文名称: (2-cyanoethyl)hydrazone of 4-(benzyloxy)benzaldehyde
• 英文别名: 4-(Benzyloxy)benzaldehyde (2-cyanoethyl)hydrazone；3-[2-[(4-phenylmethoxyphenyl)methylidene]hydrazinyl]propanenitrile
• CAS: 170300-76-2
• 化学式: C₁₇H₁₇N₃O
• 分子量: 279.341
• InChiKey: KLAJUHPSZLVWQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 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：
  57.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  氯甲酸乙酯 、 (2-cyanoethyl)hydrazone of 4-(benzyloxy)benzaldehyde 在 吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以71%的产率得到ethyl N-(2-cyanoethyl)-N-[(4-phenylmethoxyphenyl)methylideneamino]carbamate
  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-氰基乙基肼 生成 (2-cyanoethyl)hydrazone of 4-(benzyloxy)benzaldehyde
  参考文献：
  名称：

  Monoamine oxidase B inhibitors, processes for their preparation and use

  摘要：

  式(I)中的新型单胺氧化酶B抑制剂，其中R.sub.1=dbd.H，或是可选取代的苄氧基或苯乙氧基；p=0-3；R.sub.3=dbd.H，或是CN，OH，CCH基团，C.sub.1-C.sub.3烷氧基羰基基团，或是C.sub.1-C.sub.3烷基化的氰甲基基团；R.sub.2=dbd.H或是C.sub.1-C.sub.3烷基；n=0或1；如果n=0，R.sub.4是C.sub.1-C.sub.3烷基或C.sub.1-C.sub.3烷氧基群，而如果n=1，y=1且R.sub.4是C.sub.1-C.sub.3烷基，C.sub.1-C.sub.3烷氧基群或苯基。本发明还涉及制备所述新型抑制剂的方法以及其治疗用途。##STR1##

  公开号：

  US05811456A1