(2-cyanoethyl)hydrazone of benzaldehyde | 1202-58-0

• 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: (2-cyanoethyl)hydrazone of benzaldehyde
• 英文别名: N-Benzyliden-N'-β-cyanethyl-hydrazin；Benzaldehyd-N-(2-cyan-aethyl)-hydrazon；Benzaldehyde (2-cyanoethyl)hydrazone；3-(2-benzylidenehydrazinyl)propanenitrile
• CAS: 1202-58-0
• 化学式: C₁₀H₁₁N₃
• 分子量: 173.217
• InChiKey: NLUJGOPPANLICK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-cyanoethyl)hydrazone of benzaldehyde 在 sodium hydroxide 作用下， 反应 5.0h， 生成 1-苄基-1H-吡唑-5-胺
  参考文献：
  名称：

  [EN] TRIAZOLOPYRIDAZINE
  [FR] DÉRIVÉS TRIAZOLOPYRIDAZINES

  摘要：

  本发明涵盖了一般式(I)中的化合物，其中基团R1至R3具有声明和规范中给出的含义。本发明的化合物适用于治疗由过度或异常细胞增殖特征的疾病，包括含有这些化合物的药物制剂以及它们作为药物的用途。

  公开号：

  WO2014076146A1
• 作为产物：
  描述：

  苯甲醛 、 2-氰基乙基肼 以 甲苯 为溶剂， 反应 0.17h， 生成 (2-cyanoethyl)hydrazone of benzaldehyde
  参考文献：
  名称：

  3-与α-氧-乙烯酮的1，3-偶极环加成反应：吡唑烷二酮的三组分立体选择性入口和原始的螺氧杂吲哚类

  摘要：

  立体定义的单环，螺双环和双-螺旋三环吡唑并烷-3-酮可通过三组分反应高效制备，该反应涉及从中获得的偶氮甲亚胺与原位生成的α-氧代-乙烯酮双极性亲和剂的1,3-偶极环加成反应。该反应允许在单个催化剂/无添加剂，高度原子经济的转化中以优异的非对映选择性创建四个共价键和两个连续的手性季中心。从基本的观点来看，该反应在1，3-偶极环加成中引入α-氧代-乙烯酮作为有效的偶极亲和性。

  DOI：

  10.1021/ol2016669

文献信息

• TRIAZOLOPYRIDAZINE
  申请人：ENGELHARDT Harald

  公开号：US20140135336A1

  公开（公告）日：2014-05-15

  Disclosed are compounds of general formula (I) wherein the groups R 1 to R 3 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.

  揭示了一般式(I)的化合物，其中基团R1至R3具有索赔和说明中所给的含义。本发明的化合物适用于治疗以细胞过度或异常增殖为特征的疾病，包括含有这些化合物的药物制剂以及它们作为药物的用途。
• 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##
• Approach to the Library of Fused Pyridine-4-carboxylic Acids by Combes-Type Reaction of Acyl Pyruvates and Electron-Rich Amino Heterocycles
  作者：Dmitriy M. Volochnyuk、Sergey V. Ryabukhin、Andrey S. Plaskon、Yuri V. Dmytriv、Oleksandr O. Grygorenko、Pavel K. Mykhailiuk、Dmitriy G. Krotko、Alexei Pushechnikov、Andrey A. Tolmachev

  DOI：10.1021/cc100040q

  日期：2010.7.12

  A library of fused pyridine-4-carboxylic acids (including pyrazolo[3,4-b]pyridines, isoxazolo[5,4-b]pyridines, furo[2,3-b]pyridines, thieno[2,3-b]pyridines, and pyrido[2,3-d]pyrimidines) was generated by Combes-type reaction of acyl pyruvates and electron-rich amino heterocycles followed by hydrolysis of the ester. The library members were also demonstrated to undergo the standard combinatorial transformations including amide coupling and esterification, as well as less common heterocyclizations to 1,2,4-triazoles and 1,2,4-oxadiazoles.
• Hoehn,H., Zeitschrift fur Chemie, 1970, vol. 10, p. 386 - 388
  作者：Hoehn,H.

  DOI：——

  日期：——
• 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.