4-[(2,5-dimethoxyphenyl)methyl]-6H-pyrrolo[1,2-a][1,4]benzodiazepine | 1027045-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 4-[(2,5-dimethoxyphenyl)methyl]-6H-pyrrolo[1,2-a][1,4]benzodiazepine
• CAS: 1027045-32-4
• 化学式: C₂₁H₂₀N₂O₂
• 分子量: 332.402
• InChiKey: AOVORRCLZPVVJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(2,5-dimethoxyphenyl)methyl]-6H-pyrrolo[1,2-a][1,4]benzodiazepine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 4-[(2,5-dimethoxyphenyl)methyl]-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepine
  参考文献：
  名称：

  Pyrrolobenzodiazepines with antinociceptive activity: synthesis and pharmacological activities

  摘要：

  The synthesis of some N-[2-(1H-pyrrol-1-yl)benzyl] arylacetamides and new 4-arylmethyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepines, as their conformationally restricted analogues is reported. The reduction of arylacetamides and N-methylation of pyrrolobenzodiazepines led to the corresponding N-[2-(1H-pyrrol-1-yl)benzyl]arylethylamines and the 4-arylmethyl-5-methyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepines, respectively. The new compounds were subjected to pharmacological tests for evaluation of antinociceptive effects. Neurobehavioural assays were also carried out on selected compounds to acquire data on neurotoxicity. Among the derivatives tested, arylacetamides 7b and 7e and 4-(4-methoxybenzyl)-5-methyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepine 10d were the most active derivatives in antinociceptive assays, showing high significance in both hot-plate and acetic-acid-induced writhing tests in mice without sedative or myorelaxant effects.

  DOI：

  10.1016/0223-5234(96)88274-2
• 作为产物：
  描述：

  2-(1-吡咯基)苄胺 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氯氧磷 作用下， 反应 4.0h， 生成 4-[(2,5-dimethoxyphenyl)methyl]-6H-pyrrolo[1,2-a][1,4]benzodiazepine
  参考文献：
  名称：

  Pyrrolobenzodiazepines with antinociceptive activity: synthesis and pharmacological activities

  摘要：

  The synthesis of some N-[2-(1H-pyrrol-1-yl)benzyl] arylacetamides and new 4-arylmethyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepines, as their conformationally restricted analogues is reported. The reduction of arylacetamides and N-methylation of pyrrolobenzodiazepines led to the corresponding N-[2-(1H-pyrrol-1-yl)benzyl]arylethylamines and the 4-arylmethyl-5-methyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepines, respectively. The new compounds were subjected to pharmacological tests for evaluation of antinociceptive effects. Neurobehavioural assays were also carried out on selected compounds to acquire data on neurotoxicity. Among the derivatives tested, arylacetamides 7b and 7e and 4-(4-methoxybenzyl)-5-methyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepine 10d were the most active derivatives in antinociceptive assays, showing high significance in both hot-plate and acetic-acid-induced writhing tests in mice without sedative or myorelaxant effects.

  DOI：

  10.1016/0223-5234(96)88274-2

文献信息

• Pyrrolobenzodiazepines with antinociceptive activity: synthesis and pharmacological activities
  作者：A Mai、R Di Santo、S Massa、M Artico、GC Pantaleoni、R Giorgi、MF Coppolino、A Barracchini

  DOI：10.1016/0223-5234(96)88274-2

  日期：1995.1

  The synthesis of some N-[2-(1H-pyrrol-1-yl)benzyl] arylacetamides and new 4-arylmethyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepines, as their conformationally restricted analogues is reported. The reduction of arylacetamides and N-methylation of pyrrolobenzodiazepines led to the corresponding N-[2-(1H-pyrrol-1-yl)benzyl]arylethylamines and the 4-arylmethyl-5-methyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepines, respectively. The new compounds were subjected to pharmacological tests for evaluation of antinociceptive effects. Neurobehavioural assays were also carried out on selected compounds to acquire data on neurotoxicity. Among the derivatives tested, arylacetamides 7b and 7e and 4-(4-methoxybenzyl)-5-methyl-5,6-dihydro-4H-pyrrolo[1,2-a][1,4]benzodiazepine 10d were the most active derivatives in antinociceptive assays, showing high significance in both hot-plate and acetic-acid-induced writhing tests in mice without sedative or myorelaxant effects.