(3,4-dimethoxy-phenethyl)-(3-nitro-benzyliden)-amine | 1503-46-4

• 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: (3,4-dimethoxy-phenethyl)-(3-nitro-benzyliden)-amine
• 英文别名: (3,4-Dimethoxy-phenaethyl)-(3-nitro-benzyliden)-amin；N-[2-(3,4-dimethoxyphenyl)ethyl]-1-(3-nitrophenyl)methanimine
• CAS: 1503-46-4
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: IJSNTUIMUMRSKV-UHFFFAOYSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  462.5±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3,4-dimethoxy-phenethyl)-(3-nitro-benzyliden)-amine 在 三氟乙酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 90.0 ℃ 、1.38 MPa 条件下， 反应 0.08h， 生成 6,7-dimethoxy-1-(3-nitrophenyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis and evaluation of pharmacological profile of 1-aryl-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamides

  摘要：

  In previous studies we identified several 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives displaying potent anticonvulsant effects in different animal models of epilepsy. With the aim to deepen the structure-activity relationships (SAR) for this class of compounds and identify novel anticonvulsant agents we synthesized a series of 1-aryl-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamides. The new compounds incorporate the main features of the above-mentioned anticonvulsants and a sulfonamide function capable to inhibit the enzyme carbonic anhydrase (CA, EC 4.2.1.1), which represents an attractive target in epilepsy. Pharmacological effects were evaluated in vivo against audiogenic seizures in DBA/2 mice and in vitro against several CA isoforms. Some of the new molecules showed anticonvulsant properties better than topiramate, but weak inhibitory activity and low selectivity in enzymatic assay. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.066
• 作为产物：
  描述：

  间硝基苯甲醛 、 3,4-二甲氧基苯乙胺 90.0 ℃ 、1.38 MPa 条件下， 反应 0.08h， 生成 (3,4-dimethoxy-phenethyl)-(3-nitro-benzyliden)-amine
  参考文献：
  名称：

  Synthesis and evaluation of pharmacological profile of 1-aryl-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamides

  摘要：

  In previous studies we identified several 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives displaying potent anticonvulsant effects in different animal models of epilepsy. With the aim to deepen the structure-activity relationships (SAR) for this class of compounds and identify novel anticonvulsant agents we synthesized a series of 1-aryl-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamides. The new compounds incorporate the main features of the above-mentioned anticonvulsants and a sulfonamide function capable to inhibit the enzyme carbonic anhydrase (CA, EC 4.2.1.1), which represents an attractive target in epilepsy. Pharmacological effects were evaluated in vivo against audiogenic seizures in DBA/2 mice and in vitro against several CA isoforms. Some of the new molecules showed anticonvulsant properties better than topiramate, but weak inhibitory activity and low selectivity in enzymatic assay. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.066

文献信息

• SYNTHESIS OF TETRAHYDROISOQUINOLINE DERIVATIVES
  作者：EUGENE C. WEINBACH、WALTER H. HARTUNG

  DOI：10.1021/jo01149a037

  日期：1950.5
• Synthesis and evaluation of pharmacological profile of 1-aryl-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamides
  作者：Rosaria Gitto、Stefania Ferro、Stefano Agnello、Laura De Luca、Giovanbattista De Sarro、Emilio Russo、Daniela Vullo、Claudiu T. Supuran、Alba Chimirri

  DOI：10.1016/j.bmc.2009.03.066

  日期：2009.5

  In previous studies we identified several 1-aryl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives displaying potent anticonvulsant effects in different animal models of epilepsy. With the aim to deepen the structure-activity relationships (SAR) for this class of compounds and identify novel anticonvulsant agents we synthesized a series of 1-aryl-6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-sulfonamides. The new compounds incorporate the main features of the above-mentioned anticonvulsants and a sulfonamide function capable to inhibit the enzyme carbonic anhydrase (CA, EC 4.2.1.1), which represents an attractive target in epilepsy. Pharmacological effects were evaluated in vivo against audiogenic seizures in DBA/2 mice and in vitro against several CA isoforms. Some of the new molecules showed anticonvulsant properties better than topiramate, but weak inhibitory activity and low selectivity in enzymatic assay. (C) 2009 Elsevier Ltd. All rights reserved.