N-(4-methoxy-benzyl)-2-bromo-5-chloroaniline | 671207-58-2

• 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: N-(4-methoxy-benzyl)-2-bromo-5-chloroaniline
• 英文别名: 2-bromo-5-chloro-N-[(4-methoxyphenyl)methyl]aniline
• CAS: 671207-58-2
• 化学式: C₁₄H₁₃BrClNO
• mdl: MFCD25094104
• 分子量: 326.62
• InChiKey: JKCXNWCTXHGRCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-methoxy-benzyl)-2-bromo-5-chloroaniline 在 四(三苯基膦)钯 吡啶 、 甲酸 、 硫酸 、 1-羟基苯并三唑 、 臭氧 、 苯甲醚 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 33.5h， 生成 (E)-2-(3-amino-8-chloro-2-oxo-1,2,3,4-tetrahydrobenzo[b]azepin-5-ylidene)-N-phenyl-acetamide
  参考文献：
  名称：

  Benzoazepine derivative as potent antagonists of the glycine binding site associated to the NMDA receptor

  摘要：

  A series of benzoazepine derivatives, bearing suitable substituents at the C-3 position, was designed and evaluated by superimposition with the pharmacophore model of the glycine binding site. To fully explore the SAR of this class of compounds and to allow the preparation of new different compounds at the C-3 position, appropriate synthetic routes were set up. The benzoazepines were evaluated in terms of in vitro affinity using [3H]glycine binding assay and in vivo potency by inhibition of convulsions induced by N-methyl-D-aspartate (NMDA) in mice. This further analysis confirmed the preliminary results previously reported and that compound 27 is the most promising compound (Ki=32 nM, ED(50)=0.09 mg/kg, i.v.) in this series. Significant neuroprotective effect was observed after both pre- and post-ischaemia administration in the MCAo model. In particular, after post-ischaemia administration, it was found to be still effective when the administration was delayed up to 6 h after occlusion of the middle cerebral artery.

  DOI：

  10.1016/s0014-827x(03)00166-6
• 作为产物：
  描述：

  2-溴-5-氯硝基苯 在 铁粉 、 溶剂黄146 、 sodium iodide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 N-(4-methoxy-benzyl)-2-bromo-5-chloroaniline
  参考文献：
  名称：

  Benzoazepine derivative as potent antagonists of the glycine binding site associated to the NMDA receptor

  摘要：

  A series of benzoazepine derivatives, bearing suitable substituents at the C-3 position, was designed and evaluated by superimposition with the pharmacophore model of the glycine binding site. To fully explore the SAR of this class of compounds and to allow the preparation of new different compounds at the C-3 position, appropriate synthetic routes were set up. The benzoazepines were evaluated in terms of in vitro affinity using [3H]glycine binding assay and in vivo potency by inhibition of convulsions induced by N-methyl-D-aspartate (NMDA) in mice. This further analysis confirmed the preliminary results previously reported and that compound 27 is the most promising compound (Ki=32 nM, ED(50)=0.09 mg/kg, i.v.) in this series. Significant neuroprotective effect was observed after both pre- and post-ischaemia administration in the MCAo model. In particular, after post-ischaemia administration, it was found to be still effective when the administration was delayed up to 6 h after occlusion of the middle cerebral artery.

  DOI：

  10.1016/s0014-827x(03)00166-6

文献信息

• Asymmetric construction of quaternary α-nitro amides by palladium-catalyzed C(sp³)–H arylation
  作者：Wei-Xin Kong、Shi-Jing Xie、Chen-Yao-Zi Cao、Chao-Wei Zhang、Chuanyong Wang、Wei-Liang Duan

  DOI：10.1039/c9cc07854a

  日期：——

  Pd-Catalyzed enantioselective C(sp3)-H arylation of N-(o-Br-aryl) anilides has been disclosed, and quaternary α-nitro amides were constructed with up to 98% ee. The presence of the nitro group on the substrate enables the progress of the reaction and the ready transformation of the product to optically active quaternary amino acid derivatives.

  已经公开了N-（邻-Br-芳基）苯胺的Pd催化的对映选择性C（sp3）-H芳基化反应，并且构建了具有高达98％ee的季α-硝基酰胺。底物上硝基的存在使反应得以进行，并使产物易于转化为旋光性季氨基酸衍生物。
• Benzoazepine derivative as potent antagonists of the glycine binding site associated to the NMDA receptor
  作者：Romano Di Fabio、Fabrizio Micheli、Davide Baraldi、Barbara Bertani、Nadia Conti、Giovanna Dal Forno、Aldo Feriani、Daniele Donati、Carla Marchioro、Tommaso Messeri、Andrea Missio、Alessandra Pasquarello、Giorgio Pentassuglia、Domenica A. Pizzi、Stefano Provera、Anna M. Quaglia、Fabio M. Sabbatini

  DOI：10.1016/s0014-827x(03)00166-6

  日期：2003.9

  A series of benzoazepine derivatives, bearing suitable substituents at the C-3 position, was designed and evaluated by superimposition with the pharmacophore model of the glycine binding site. To fully explore the SAR of this class of compounds and to allow the preparation of new different compounds at the C-3 position, appropriate synthetic routes were set up. The benzoazepines were evaluated in terms of in vitro affinity using [3H]glycine binding assay and in vivo potency by inhibition of convulsions induced by N-methyl-D-aspartate (NMDA) in mice. This further analysis confirmed the preliminary results previously reported and that compound 27 is the most promising compound (Ki=32 nM, ED(50)=0.09 mg/kg, i.v.) in this series. Significant neuroprotective effect was observed after both pre- and post-ischaemia administration in the MCAo model. In particular, after post-ischaemia administration, it was found to be still effective when the administration was delayed up to 6 h after occlusion of the middle cerebral artery.