4-amino-1-benzyl-5-methyl-2,5-dihydro-pyrrole-3-carbonitrile | 3510-34-7

• 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: 4-amino-1-benzyl-5-methyl-2,5-dihydro-pyrrole-3-carbonitrile
• 英文别名: 3-amino-4-cyano-1-benzyl-2-methyl-3-pyrroline；3-Amino-1-benzyl-4-cyan-2-methyl-Δ³-pyrrolidin；3-Amino-4-cyan-2-methyl-1-benzyl-Δ³-pyrrolin；3-Amino-1-benzyl-4-cyan-2-methyl-3-pyrrolin；4-amino-1-benzyl-5-methyl-2,5-dihydropyrrole-3-carbonitrile
• CAS: 3510-34-7
• 化学式: C₁₃H₁₅N₃
• 分子量: 213.282
• InChiKey: POZVNJGZSIULOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-amino-1-benzyl-5-methyl-2,5-dihydro-pyrrole-3-carbonitrile 在 N-甲基吡咯烷酮 、 sodium ethanolate 作用下， 反应 19.0h， 生成 11-Benzyl-4-(2-fluorophenyl)-10-methyl-3,5,6,8,11-pentazatricyclo[7.3.0.02,6]dodeca-1(9),2,4-trien-7-one
  参考文献：
  名称：

  Anxiolytic properties of certain annelated [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones

  摘要：

  Modification of the benzodiazepine (BZ) receptor binding template 2-aryl[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one by replacement of the annelated benzene ring with various alicyclic and heterocyclic moieties led to novel structures with potent BZ receptor binding affinity. High affinity was found in some cycloalkyl-annelated [1,2,4]triazolo-[1,5-c]pyrimidin-5(6H)-ones and in some 7,8,9,10-tetrahydropyrido[3,4-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones, in which the degree of activity was strongly dependent on the N-substituent in the 9-position. Nine compounds with BZ receptor IC50 binding affinity values equal or superior to diazepam were evaluated in secondary screening. One of these, 9-benzyl-2-phenyl-7,8,9,10-tetrahydropyrido[3,4-e]?? [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one, showed good activity in rats as a potential anxiolytic agent without sedative liability. However, it increased the rotorod deficit produced by ethanol at anxiolytic doses, an indication of alcohol interaction. Thus, none of the compounds showed an advantage over CGS 9896 (Yokoyama et al. J. Med. Chem. 1982, 25, 337-339), which is free of sedative and alcohol interaction potential as measured by the test procedures described.

  DOI：

  10.1021/jm00113a032
• 作为产物：
  描述：

  N-(1-cyanoethyl)-N-(2-cyanoethyl)benzylamine 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 生成 4-amino-1-benzyl-5-methyl-2,5-dihydro-pyrrole-3-carbonitrile
  参考文献：
  名称：

  Anxiolytic properties of certain annelated [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones

  摘要：

  Modification of the benzodiazepine (BZ) receptor binding template 2-aryl[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one by replacement of the annelated benzene ring with various alicyclic and heterocyclic moieties led to novel structures with potent BZ receptor binding affinity. High affinity was found in some cycloalkyl-annelated [1,2,4]triazolo-[1,5-c]pyrimidin-5(6H)-ones and in some 7,8,9,10-tetrahydropyrido[3,4-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones, in which the degree of activity was strongly dependent on the N-substituent in the 9-position. Nine compounds with BZ receptor IC50 binding affinity values equal or superior to diazepam were evaluated in secondary screening. One of these, 9-benzyl-2-phenyl-7,8,9,10-tetrahydropyrido[3,4-e]?? [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one, showed good activity in rats as a potential anxiolytic agent without sedative liability. However, it increased the rotorod deficit produced by ethanol at anxiolytic doses, an indication of alcohol interaction. Thus, none of the compounds showed an advantage over CGS 9896 (Yokoyama et al. J. Med. Chem. 1982, 25, 337-339), which is free of sedative and alcohol interaction potential as measured by the test procedures described.

  DOI：

  10.1021/jm00113a032

文献信息

• Pyrrolidines containing two primary amino groups and process for their
  申请人：Ciba-Geigy Corporation

  公开号：US03957820A1

  公开（公告）日：1976-05-18

  The invention relates to 3-amino-4-aminomethyl-pyrrolidines which contain, in the 1-position of the heterocyclic ring, organic radicals as substituents, and in which also the H-atom in the 2-position of the heterocyclic ring can be substituted by an organic radical. The invention also relates to the preparation of these pyrrolidines by catalytic hydrogenation of the corresponding 3-amino-4-cyano-3-pyrrolines. Hydrogenation is preferably performed in the presence of NH.sub.3. The amines according to the invention are suitable as curing agents for epoxide resins, as reactants for isocyanates, and as starting substances for polyamides.

  该发明涉及3-氨基-4-氨甲基-吡咯烷，其在杂环环的1-位置含有有机基作为取代基，在杂环环的2-位置的H原子也可以被有机基取代。该发明还涉及通过催化氢化相应的3-氨基-4-氰基-3-吡咯烯制备这些吡咯烷。氢化最好在NH.sub.3存在下进行。根据该发明的胺类适用作为环氧树脂的固化剂，作为异氰酸酯的反应物，以及作为聚酰胺的起始物质。
• US3957820A
  申请人：——

  公开号：US3957820A

  公开（公告）日：1976-05-18
• Anxiolytic properties of certain annelated [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones
  作者：John E. Francis、Debra A. Bennett、James L. Hyun、Stephen L. Rovinski、Caryl L. Amrick、Patricia S. Loo、Deborah Murphy、Robert F. Neale、Douglas E. Wilson

  DOI：10.1021/jm00113a032

  日期：1991.9

  Modification of the benzodiazepine (BZ) receptor binding template 2-aryl[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one by replacement of the annelated benzene ring with various alicyclic and heterocyclic moieties led to novel structures with potent BZ receptor binding affinity. High affinity was found in some cycloalkyl-annelated [1,2,4]triazolo-[1,5-c]pyrimidin-5(6H)-ones and in some 7,8,9,10-tetrahydropyrido[3,4-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones, in which the degree of activity was strongly dependent on the N-substituent in the 9-position. Nine compounds with BZ receptor IC50 binding affinity values equal or superior to diazepam were evaluated in secondary screening. One of these, 9-benzyl-2-phenyl-7,8,9,10-tetrahydropyrido[3,4-e]?? [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one, showed good activity in rats as a potential anxiolytic agent without sedative liability. However, it increased the rotorod deficit produced by ethanol at anxiolytic doses, an indication of alcohol interaction. Thus, none of the compounds showed an advantage over CGS 9896 (Yokoyama et al. J. Med. Chem. 1982, 25, 337-339), which is free of sedative and alcohol interaction potential as measured by the test procedures described.