3-(Benzotriazol-1-ylmethylamino)benzonitrile | 1026573-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 3-(Benzotriazol-1-ylmethylamino)benzonitrile
• CAS: 1026573-90-9
• 化学式: C₁₄H₁₁N₅
• 分子量: 249.275
• InChiKey: XIQOKERJDPVEHF-UHFFFAOYSA-N

物化性质

• 沸点：
  512.7±35.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(Benzotriazol-1-ylmethylamino)benzonitrile 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 96.0h， 生成 2-methyl-N-[[3-(methylamino)phenyl]methyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Anxiolytic activity of analogues of 4-benzylamino-2-methyl-7H-pyrrolo[2,3-d]pyrimidines

  摘要：

  An extensive series of analogues of the lead anxiolytic 4-benzylamino-2-methylpyrrolo[2,3-d]pyrimidine 1 was synthesized and evaluated in the Geller-Seifter conflict test for anxiolytic activity to discover a less toxic derivative. Analysis of the SAR revealed that the most potent compounds were those with meta substituents on the benzylamino ring. In this group the most promising derivatives were 4-[bis(3,5-dimethylamino)]benzylamino-2-methyl-7H-pyrrolo[2,3-d]pyrimidine 12 and 4-(3,5-dimethylbenzylamino)-2-methyl-7H-pyrrolo [2,3-d]pyrimidine 24. Potential metabolites of 12 were synthesized and checked for their anxiolytic activity. Less toxic analogues of the second lead 24 were prepared by extending the alkyl groups attached to the benzene ring moiety. The addition of a fluoro substituent to the benzene moiety in the extended alkyl chain analogue 4-(3,5-diethyl-2-fluorobenzylamino)-2-methyl-7H-pyrrolo[2,3-d]pyrimidine 34 resulted in a compound with a longer duration of activity relative to its analogue 4-(3,5-diethylbenzylamino)-2-methyl-7H-pyrrolo[2,3-d]pyrimidine 26. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80003-2
• 作为产物：
  描述：

  T406石油添加剂 、 聚合甲醛 、 间氨基苯甲腈 以 乙醇 、 水 为溶剂， 反应 23.0h， 以77%的产率得到3-(Benzotriazol-1-ylmethylamino)benzonitrile
  参考文献：
  名称：

  Anxiolytic activity of analogues of 4-benzylamino-2-methyl-7H-pyrrolo[2,3-d]pyrimidines

  摘要：

  An extensive series of analogues of the lead anxiolytic 4-benzylamino-2-methylpyrrolo[2,3-d]pyrimidine 1 was synthesized and evaluated in the Geller-Seifter conflict test for anxiolytic activity to discover a less toxic derivative. Analysis of the SAR revealed that the most potent compounds were those with meta substituents on the benzylamino ring. In this group the most promising derivatives were 4-[bis(3,5-dimethylamino)]benzylamino-2-methyl-7H-pyrrolo[2,3-d]pyrimidine 12 and 4-(3,5-dimethylbenzylamino)-2-methyl-7H-pyrrolo [2,3-d]pyrimidine 24. Potential metabolites of 12 were synthesized and checked for their anxiolytic activity. Less toxic analogues of the second lead 24 were prepared by extending the alkyl groups attached to the benzene ring moiety. The addition of a fluoro substituent to the benzene moiety in the extended alkyl chain analogue 4-(3,5-diethyl-2-fluorobenzylamino)-2-methyl-7H-pyrrolo[2,3-d]pyrimidine 34 resulted in a compound with a longer duration of activity relative to its analogue 4-(3,5-diethylbenzylamino)-2-methyl-7H-pyrrolo[2,3-d]pyrimidine 26. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80003-2

文献信息

• Anxiolytic activity of analogues of 4-benzylamino-2-methyl-7H-pyrrolo[2,3-d]pyrimidines
  作者：Eric A. Meade、Marcos Sznaidman、Gerald T. Pollard、Lilia M. Beauchamp、James L. Howard

  DOI：10.1016/s0223-5234(98)80003-2

  日期：1998.6

  An extensive series of analogues of the lead anxiolytic 4-benzylamino-2-methylpyrrolo[2,3-d]pyrimidine 1 was synthesized and evaluated in the Geller-Seifter conflict test for anxiolytic activity to discover a less toxic derivative. Analysis of the SAR revealed that the most potent compounds were those with meta substituents on the benzylamino ring. In this group the most promising derivatives were 4-[bis(3,5-dimethylamino)]benzylamino-2-methyl-7H-pyrrolo[2,3-d]pyrimidine 12 and 4-(3,5-dimethylbenzylamino)-2-methyl-7H-pyrrolo [2,3-d]pyrimidine 24. Potential metabolites of 12 were synthesized and checked for their anxiolytic activity. Less toxic analogues of the second lead 24 were prepared by extending the alkyl groups attached to the benzene ring moiety. The addition of a fluoro substituent to the benzene moiety in the extended alkyl chain analogue 4-(3,5-diethyl-2-fluorobenzylamino)-2-methyl-7H-pyrrolo[2,3-d]pyrimidine 34 resulted in a compound with a longer duration of activity relative to its analogue 4-(3,5-diethylbenzylamino)-2-methyl-7H-pyrrolo[2,3-d]pyrimidine 26. (C) Elsevier, Paris.