N-(4''-fluorobenzyl)-2-nitroaniline | 100460-79-5

• 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''-fluorobenzyl)-2-nitroaniline
• 英文别名: N-(4-fluorobenzyl)-2-nitroaniline；N-(4-fluorobenzyl) 2-nitroaniline；Benzenemethanamine, 4-fluoro-N-(2-nitrophenyl)-；N-[(4-fluorophenyl)methyl]-2-nitroaniline
• CAS: 100460-79-5
• 化学式: C₁₃H₁₁FN₂O₂
• mdl: MFCD04107855
• 分子量: 246.241
• InChiKey: HDDNMPHXSUSADO-UHFFFAOYSA-N

物化性质

• 熔点：
  76-77 °C(Solv: ethanol (64-17-5))
• 沸点：
  386.7±27.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4''-fluorobenzyl)-2-nitroaniline 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.0h， 生成 9-(4-fluorobenzyl)-2,9-dihydro-3H-imidazo[1,2-a]benzimidazole
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,3-dihydroimidazo[1,2-a]benzimidazole derivatives against Leishmania donovani and Trypanosoma cruzi

  摘要：

  A high-throughput (HTS) and high-content screening (HCS) campaign of a commercial library identified 2,3-dihydroimidazo[1,2-a]benzimidazole analogues as a novel class of anti-parasitic agents. A series of synthetic derivatives were evaluated for their in vitro anti-leishmanial and anti-trypanosomal activities against Leishmania donovani and Trypanosoma cruzi, which have been known as the causative parasites for visceral leishmaniasis and Chagas disease, respectively. In the case of Leishmania, the compounds were tested in both intracellular amastigote and extracellular promastigote assays. Compounds 4 and 24 showed promising anti-leishmanial activity against intracellular L. donovani (3.05 and 5.29 μM, respectively) and anti-trypanosomal activity against T. cruzi (1.10 and 2.10 μM, respectively) without serious cytotoxicity toward THP-1 and U2OS cell lines.

  DOI：

  10.1016/j.ejmech.2014.07.038
• 作为产物：
  描述：

  4-氟氯苄 以 丁酮 为溶剂， 生成 N-(4''-fluorobenzyl)-2-nitroaniline
  参考文献：
  名称：

  Derivatives of terbutylphenyl-1-amino-4-hydroxybutane their preparation

  摘要：

  本发明涉及一般式（I）中的（4-取代苯基）4-氧基-1-氨基丁烷，其中X是氮原子或>CH-CH，R是从包括a）黄色素取代基，b）苯并咪唑取代基的群体中选择的环状取代基，以及公式（I）化合物的盐和光学异构体。本发明还涉及获得公式（I）化合物的过程和含有至少一种公式（I）化合物或其与矿物酸或有机酸盐的药物组合物，作为抗组胺剂成分的制药组合物。

  公开号：

  US05461059A1

文献信息

• Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2‐Aryldiamines
  作者：Réka J. Faggyas、Nikki L. Sloan、Ned Buijs、Andrew Sutherland

  DOI：10.1002/ejoc.201900463

  日期：2019.9

  mild conditions, using a polymer‐supported nitrite reagent and p‐tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N‐alkyl, ‐aryl, and ‐acyl ortho‐aminoanilines leading to the synthesis of N1‐substituted benzotriazoles. The synthetic utility of this one‐pot heterocyclization process was exemplified with the preparation of a

  已经开发了一种操作简单的方法，通过使用聚合物负载的亚硝酸盐试剂和对甲苯磺酸在温和条件下通过重氮化和分子内环化多种 1,2-芳基二胺来制备 N-未取代的苯并三唑。通过有效活化和环化 N-烷基、-芳基和-酰基邻-氨基苯胺，合成 N1 取代的苯并三唑，进一步证明了该方法的官能团耐受性。这种单锅杂环化过程的合成效用可以通过制备许多具有生物学和医学意义的苯并三唑支架来举例说明，包括一种 α-氨基酸类似物。
• Design, synthesis, and biological evaluation of 4-phenoxyquinoline derivatives as potent c-Met kinase inhibitor
  作者：Yifeng Yang、Yingxiu Li、Yunlei Hou、Mingze Qin、Ping Gong、Ju Liu、Yanfang Zhao

  DOI：10.1016/j.bmcl.2019.126666

  日期：2019.12

  A series of novel 4-phenoxyquinoline derivatives containing 3-oxo-3,4-dihydro-quinoxaline moiety were synthesized and evaluated for their antiproliferative activity against five human cancer cell lines (A549, H460, HT-29, MKN-45 and U87MG) in vitro. Most of the tested compounds exhibited more potent inhibitory activities than the positive control foretinib. Compound 1b, 1s and 1t were further examined

  合成了一系列包含3-oxo-3,4-dihydro-quinoxaline部分的新型4-苯氧基喹啉衍生物，并评估了它们对五种人类癌细胞系（A549，H460，HT-29，MKN-45和U87MG）的抗增殖活性在体外。大多数测试化合物均比阳性对照foretinib表现出更强的抑制活性。进一步检查化合物1b，1s和1t对c-Met激酶的抑制活性。最有前途的化合物1s（c-Met IC 50值为1.42 nM）对具有IC 50的A549，H460，HT-29，MKN45和U87MG细胞系表现出显着的细胞毒性分别为0.39μM，0.18μM，0.38μM，0.81μM。他们的初步结构-活性关系（SARs）研究表明，用环己烷取代芳环可提高其抗增殖活性。
• “All-water” chemistry of tandem N-alkylation–reduction–condensation for synthesis of N-arylmethyl-2-substituted benzimidazoles
  作者：Damodara N. Kommi、Dinesh Kumar、Rohit Bansal、Rajesh Chebolu、Asit K. Chakraborti

  DOI：10.1039/c2gc36377a

  日期：——

  also exerts a beneficial effect in the condensation of N-monobenzylated o-phenylenediamines with aldehydes. The water-assisted C–N bond formation chemistry led to metal/base-free synthesis of N-monobenzylated o-nitroanilines and N-monobenzylated o-phenylenediamines. The indispensable/advantageous role of water in the various stage of the N-alkylation–reduction–condensation process exemplifies an ‘all-water’

  设计了水辅助串联N-烷基化-还原-缩合工艺，作为一锅合成N-芳基甲基-2-取代的新合成途径苯并咪唑。 水 通过氢键介导的“亲电-亲核双重”发挥关键和必不可少的作用 激活促进邻硝基苯胺的选择性N-单苄基化，以替代基于过渡金属的C–N键形成（胺化）化学方法，并形成以区域确定的方式将取代基布置在苯并咪唑基团上的基础。水在N-单苄基化邻苯二胺与醛类。水辅助的C–N键形成化学反应导致N /单苄基化的邻硝基苯胺和N-单苄基化的邻苯二胺的无金属/碱合成。的不可或缺/有利的作用水在N-烷基化-还原-缩合过程的各个阶段中，都可以举例说明“全水”化学合成N-芳基甲基-2-取代基的过程苯并咪唑。
• [EN] BICYCLIC INHIBITORS OF CBX CHROMODOMAINS<br/>[FR] INHIBITEURS BICYCLIQUES DE CHROMODOMAINES CBX
  申请人：ICAHN SCHOOL OF MEDICINE AT MT SINAI

  公开号：WO2021061801A1

  公开（公告）日：2021-04-01

  A genus of bicyclic inhibitors of CBX chromodomains is disclosed. The compounds are of the following genus: The compounds inhibit CBX proteins and, as a consequence, they are useful for treating prostate cancer, ovarian cancer, and B-cell lymphoma.

  揭示了一种双环抑制剂CBX chromodomains的属。这些化合物属于以下属：这些化合物抑制CBX蛋白，因此它们可用于治疗前列腺癌、卵巢癌和B细胞淋巴瘤。
• A Microcapillary System for Simultaneous, Parallel Microwave-Assisted Synthesis
  作者：Eamon Comer、Michael G. Organ

  DOI：10.1002/chem.200500820

  日期：2005.12.9

  A continuous flow, microwave-assisted, parallel-capillary microreactor has been developed. Libraries of drug candidates were prepared on the milligram scale with this reactor by injecting plugs of reagents from separate syringes into common reaction capillaries, thereby producing discrete compounds in excellent yield and purity. Microwave irradiation provides the necessary energy that existing room-temperature

  已经开发了连续流动的微波辅助平行毛细管微反应器。通过将来自独立注射器的试剂塞注入常用的反应毛细管中，用该反应器以毫克规模制备候选药物库，从而以极佳的收率和纯度生产出不连续的化合物。微波辐射提供了现有的室温微反应器技术所缺乏的必要能量，以实现更高的活化势垒转化，从而在数分钟或更短的时间内产生了所需量的所需化合物。