β-<1-Benzyliden-2-acetylhydrazino>-propionitril | 17531-57-6

• 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: β-<1-Benzyliden-2-acetylhydrazino>-propionitril
• 英文别名: Benzaldehyd-N-(2-cyan-aethyl)-N-acetyl-hydrazon；Benzaldehyde acetyl(2-cyanoethyl)hydrazone；N-(benzylideneamino)-N-(2-cyanoethyl)acetamide
• CAS: 17531-57-6
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: AOIUFNLSXUSPLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰氯 、 (2-cyanoethyl)hydrazone of benzaldehyde 在 吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以54%的产率得到β-<1-Benzyliden-2-acetylhydrazino>-propionitril
  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

文献信息

• Monoamine oxidase B inhibitors, processes for their preparation and use
  申请人：Laboratoires Mayoly Spindler

  公开号：US05811456A1

  公开（公告）日：1998-09-22

  Novel monoamine oxidase B inhibitors of formula (I), wherein R.sub.1 .dbd.H, an optionally substituted benzyloxy or phenylethoxy group; p=0-3; R.sub.3 .dbd.H, a CN, OH, CCH group, a C.sub.1 -C.sub.3 alkoxy-carbonyl group, or a C.sub.1 -C.sub.3 alkylated cyanomethyl group; R.sub.2 .dbd.H or a C.sub.1 -C.sub.3 alkyl group; n=0 or 1; if n=0, R.sub.4 is a C.sub.1 -C.sub.3 alkyl group or a C.sub.1 -C.sub.3 alkoxy group, while if n=1, y=1 and R.sub.4 is a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.3 alkoxy group or a phenyl group. The invention also concerns processes for the preparation of said novel inhibitors and the therapeutic use thereof. ##STR1##

  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##
• Selective and potent monoamine oxidase type B inhibitors: substituted semicarbazones and acylhydrazones of aromatic aldehydes and ketones
  作者：S Bernard、C Paillat、T Oddos、M Seman、R Milcent

  DOI：10.1016/0223-5234(96)88258-4

  日期：1995.1

  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.