4-bromo-2-(4-methoxyphenylamino)benzoic acid | 857589-14-1

• 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-bromo-2-(4-methoxyphenylamino)benzoic acid
• 英文别名: 4-bromo-2-(4-methoxyanilino)benzoic acid；2-p-anisidino-4-bromo-benzoic acid；2-p-Anisidino-4-brom-benzoesaeure
• CAS: 857589-14-1
• 化学式: C₁₄H₁₂BrNO₃
• 分子量: 322.158
• InChiKey: MPWFSPYEGLLGTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(4-methoxyphenylamino)benzoic acid 在 四(三苯基膦)钯 、 碘 、 三乙胺 、 三氯氧磷 、 苯酚 作用下， 以 1,4-二氧六环 、 氯仿 为溶剂， 反应 14.17h， 生成 2-methoxy-9-(4-(diethyl-1-methyl)-N-butyl)amino-6-iodo acridine
  参考文献：
  名称：

  Synthesis and biological evaluation of radioiodinated quinacrine-based derivatives for SPECT imaging of Aβ plaques

  摘要：

  The aim of the present study was to characterize the binding property of quinacrine-based acridine derivatives for A beta plaques and to evaluate this series of compounds as A beta imaging probes. Quinacrine clearly stained A beta plaques in the brain sections of A beta deposition model transgenic mice (Tg2576 mice). Similarly, the quinacrine analog, 2-methoxy-9-(4-(dimethyl-1-methyl) -N-butyl) amino-6-iodo acridine (5), labeled A beta plaques in the brain slices of Tg2576 mice. In addition, [I-125]5 showed modest affinity for A beta(1-42) aggregates with a K-d value of 48 nM. Biodistribution studies using normal mice demonstrated that [I-125]5 displayed poor initial brain uptake. Next, I-125-labeled acridines without aliphatic amino groups were synthesized and characterized. Similar to quinacrine and 5, these compounds could detect A beta plaques in the brain sections of Tg2576 mice. It should be noted that the acridines showed much higher binding affinity for A beta aggregates and greater in vivo blood brain barrier permeability than [I-125]5. Among them, 13 (6-Iodo-2-methoxy-9-methylaminoacridine) and 25 (2,9-Dimethoxy-6-iodo acridine) exhibited high affinity for the A beta aggregates with K-i values of 14 and 29 nM, respectively. In the in vivo studies, [I-125]13 and [I-125]25 showed excellent initial brain uptake (3.0 and 4.4% dose/g, respectively, at 2 min) with fast washout from the brain (0.33 and 0.37% dose/g, respectively, at 60 min). These acridine derivatives are demonstrated to be promising SPECT imaging probes for amyloid in the living brain. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.020
• 作为产物：
  描述：

  4-溴-2-氯甲苯 在 硝酸 、 potassium acetate 、 铜 、 potassium carbonate 、 汞 作用下， 生成 4-bromo-2-(4-methoxyphenylamino)benzoic acid
  参考文献：
  名称：

  Magidson et al., Zhurnal Obshchei Khimii, 1938, vol. 8, p. 56,62

  摘要：

  DOI：

文献信息

• Facile synthesis of indolo[3,2-<i>a</i>]carbazoles via Pd-catalyzed twofold oxidative cyclization
  作者：Chao Yang、Kai Lin、Lan Huang、Wei-dong Pan、Sheng Liu

  DOI：10.3762/bjoc.12.243

  日期：——

  A rapid and efficient route has been developed for the synthesis of 9-methoxycarbonylindolo[3,2-a]carbazole derivatives. The key steps in this approach involved an aromatic amination and an oxidative biaryl coupling. Via the present route, indolo[3,2-a]carbazole derivatives are available in 3–4 steps based on commercially available starting materials.

  已开发出一种快速高效的合成路径，用于合成9-甲氧羰基吲哚[3,2-a]咔唑衍生物。该方法的关键步骤包括芳香族胺化和氧化联苯偶联。通过这种方法，基于商业可获得的起始物质，吲哚[3,2-a]咔唑衍生物可在3-4步内制备完成。
• Palladium- and Copper-Catalyzed Site Selective Monoamination of Dibromobenzoic Acid
  作者：Ioannis N. Houpis、Koen Weerts、Ulrike Nettekoven、Martine Canters、Hongyu Tan、Renmao Liu、Youchu Wang

  DOI：10.1002/adsc.201000800

  日期：2011.3.7

  aryl bromides to afford selective ortho‐substituted derivatives (>99:1 selectivity; 60–80% yield) in the case of copper(I) catalysis. The solvent, base and equivalents of base were important factors in the success of this reaction. Complementary selectivity was achieved with palladium catalysis where the para‐substituted derivatives were produced selectively (>99% selectivity, 70–80% yield).

  在铜（I）催化的情况下，羧酸根阴离子已被用作电子等效芳基溴的芳族胺化中的导向基团，以提供选择性的邻位取代衍生物（选择性> 99：1；产率为60-80％）。溶剂，碱和碱的当量是该反应成功的重要因素。互补催化是通过钯催化实现的，其中对位取代的衍生物是选择性产生的（> 99％的选择性，70-80％的产率）。
• DE565411
  申请人：——

  公开号：——

  公开（公告）日：——