4-bromo-2-(phenylamino)benzoic acid | 19218-86-1

• 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-(phenylamino)benzoic acid
• 英文别名: 2-anilino-4-bromobenzoic acid
• CAS: 19218-86-1
• 化学式: C₁₃H₁₀BrNO₂
• 分子量: 292.132
• InChiKey: HDDMCWXBEZYIHD-UHFFFAOYSA-N

物化性质

• 熔点：
  209.5-210.5 °C(Solv: ethanol (64-17-5))
• 沸点：
  409.2±40.0 °C(Predicted)
• 密度：
  1.586±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromo-2-(phenylamino)benzoic acid 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 [4-bromo-2-(N-methylanilino)phenyl]methanol
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of N-Methylacridones

  摘要：

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

  DOI：

  10.1021/ol400371h
• 作为产物：
  描述：

  4-溴-2-氯苯甲酸 在 copper diacetate 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 以68%的产率得到4-bromo-2-(phenylamino)benzoic acid
  参考文献：
  名称：

  Tetradentate Cyclometalated Platinum Complexes Containing 9,10-Dihydroacridine And Its Analogues

  摘要：

  适用于用作磷光发射体或延迟荧光和磷光发射体的铂络合物具有以下结构：

  公开号：

  US20150349279A1

文献信息

• Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues
  申请人：Arizona Board of Regents on behalf of Arizona State University

  公开号：US09941479B2

  公开（公告）日：2018-04-10

  Platinum complexes suitable for use as phosphorescent emitters or as delayed fluorescent and phosphorescent emitters having the following structure:

  适用于用作磷光发射剂或延迟荧光和磷光发射剂的铂配合物具有以下结构：
• 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。
• Tricyclic heterocyclic derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0471516A1

  公开（公告）日：1992-02-19

  The invention relates to tricyclic heterocyclic derivatives, or pharmaceutically-acceptable salts or in vivo hydrolysable esters thereof, which possess anti-cancer activity. The invention also relates to processes for the manufacture of said tricyclic heterocyclic derivatives, to novel pharmaceutical compositions containing them and to the use of said tricyclic heterocyclic derivatives in the manufacture of a medicament for the production of an anti-cancer effect. The invention provides an optionally substituted tricyclic heterocyclic derivative of the formula I wherein A together with the adjacent vinylene group of the 4-oxo-1,4-dihydropyrid-1-yl ring completes a benzene or pyridine ring;    R¹ and R², which may be the same or different, each is (1-4C)alkyl or (1-4C)alkoxy;    and R³ is hydrogen, (1-4C)alkyl or (1-4C)alkoxy;    or a pharmaceutically-acceptable salt or in vivo hydrolysable ester thereof.

  该发明涉及三环杂环衍生物，或其药用盐或体内可水解酯，具有抗癌活性。该发明还涉及制备所述三环杂环衍生物的方法，含有它们的新型药物组合物以及利用所述三环杂环衍生物制造抗癌药物以产生抗癌效果的用途。该发明提供了公式I的可选择取代的三环杂环衍生物，其中A与4-氧代-1,4-二氢吡啶-1-基环的相邻乙烯基团共同形成苯环或吡啶环；R¹和R²，可以相同也可以不同，分别是(1-4C)烷基或(1-4C)烷氧基；R³是氢，(1-4C)烷基或(1-4C)烷氧基；或其药用盐或体内可水解酯。
• 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）。
• Synthesis and biological evaluation of radioiodinated quinacrine-based derivatives for SPECT imaging of Aβ plaques
  作者：Takeshi Fuchigami、Nobuya Kobashi、Mamoru Haratake、Masao Kawasaki、Morio Nakayama

  DOI：10.1016/j.ejmech.2012.12.020

  日期：2013.2

  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.