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4-[(2-Aminoanilino)methyl]benzonitrile | 1261288-34-9

中文名称
——
中文别名
——
英文名称
4-[(2-Aminoanilino)methyl]benzonitrile
英文别名
——
4-[(2-Aminoanilino)methyl]benzonitrile化学式
CAS
1261288-34-9
化学式
C14H13N3
mdl
MFCD17964996
分子量
223.277
InChiKey
GNCFITFETCFVAQ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.4
  • 重原子数:
    17
  • 可旋转键数:
    3
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.071
  • 拓扑面积:
    61.8
  • 氢给体数:
    2
  • 氢受体数:
    3

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    4-[(2-Aminoanilino)methyl]benzonitrilepotassium carbonate 、 copper(I) bromide 作用下, 以 二甲基亚砜 为溶剂, 120.0 ℃ 、101.33 kPa 条件下, 反应 14.0h, 生成 4-(1H-苯并[d]咪唑-2-基)苯甲腈
    参考文献:
    名称:
    CuBr-Catalyzed Oxidation/Coupling: An Efficient and Applicable Strategy for the Synthesis of 2-Aryl Benzimidazoles from 1-Fluoro-2-nitrobenzene and Benzylamines
    摘要:
    A novel and efficient route has been developed for the synthesis of benzimidazole derivatives via ligand-free CuBr-catalyzed oxidation and cyclization of 1,2-diamines derived from 1-fluoro-2-nitrobenzene and different arylamines as starting materials.
    DOI:
    10.1080/00397911.2014.971971
  • 作为产物:
    描述:
    对氰基溴化苄 在 palladium 10% on activated carbon 、 氢气potassium carbonate 作用下, 以 甲醇N,N-二甲基甲酰胺 为溶剂, 反应 7.0h, 生成 4-[(2-Aminoanilino)methyl]benzonitrile
    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
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文献信息

  • One-pot synthesis of benzimidazoles from gem-dibromomethylarenes using o-diaminoarenes
    作者:Chandrappa Siddappa、Vinaya Kambappa、Ananda Kumar C. Siddegowda、Kanchugarakoppal S. Rangappa
    DOI:10.1016/j.tetlet.2010.09.080
    日期:2010.12
    A one-pot synthesis of benzimidazoles from gem-dibromomethylarenes is described. The reaction shows the method to prepare a variety of benzimidazole analogues with excellent yield.
    描述了从宝石-二溴甲基芳烃一锅合成苯并咪唑。该反应显示出以优异的产率制备各种苯并咪唑类似物的方法。
  • Activation of Ethanol via Conjunction of a Photocatalyst and a HAT Reagent for the Synthesis of Benzimidazoles
    作者:Saloni Kumari、Abhisek Joshi、Ishani Borthakur、Sabuj Kundu
    DOI:10.1021/acs.joc.3c00674
    日期:2023.8.18
    aliphatic alcohols for the synthesis of differently functionalized benzimidazoles under mild conditions is disclosed. The interplay of a photocatalyst and a HAT reagent facilitated the activation of aliphatic alcohols. A wide array of diamines with different functional groups were well tolerated, and the protocol was also extended to N-substituted diamines for the synthesis of industrially important
    乙醇向增值化学品的转变具有巨大的潜力。然而,由于乙醇的脱氢能较高,通常需要苛刻的反应条件来进行乙醇的官能化。本文公开了一种无金属光介导的具有挑战性的乙醇和高级脂肪醇的活化,用于在温和条件下合成不同官能化的苯并咪唑。光催化剂和 HAT 试剂的相互作用促进了脂肪醇的活化。具有不同官能团的多种二胺具有良好的耐受性,并且该方案还扩展到N-取代的二胺,用于合成工业上重要的苯并咪唑。基于各种机理研究提出了可能的催化循环。
  • Benzimidazole derivatives and their uses
    申请人:TEIJIN PHARMA LIMITED
    公开号:US11332459B2
    公开(公告)日:2022-05-17
    The present invention relates to inhibitors of Transient Receptor Potential Channel 6 (TRPC6) protein activity. The present invention provides a compound of formula (I) or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising a compound of the invention, a method for manufacturing compounds of the invention and therapeutic uses thereof.
    本发明涉及瞬时受体电位通道 6(TRPC6)蛋白活性的抑制剂。本发明提供了式(I)化合物或其药学上可接受的盐、包含本发明化合物的药物组合物、制造本发明化合物的方法及其治疗用途。
  • Discovery of novel, orally available benzimidazoles as melanin concentrating hormone receptor 1 (MCHR1) antagonists
    作者:Pradip K. Sasmal、Sanjita Sasmal、P. Tirumala Rao、B. Venkatesham、M. Roshaiah、Chandrasekhar Abbineni、Ish Khanna、Vikram P. Jadhav、J. Suresh、Rashmi Talwar、Syed Muzeeb、Jean-Marie Receveur、Thomas M. Frimurer、Øystein Rist、Lisbeth Elster、Thomas Högberg
    DOI:10.1016/j.bmcl.2010.07.086
    日期:2010.9
    Melanin concentrating hormone (MCH) is an important mediator of energy homeostasis and plays role in several disorders such as obesity, stress, depression and anxiety. The synthesis and biological evaluation of novel benzimidazole derivatives as MCHR1 antagonists are described. The in vivo proof of principle for weight loss with a lead compound from this series is exemplified. (c) 2010 Elsevier Ltd. All rights reserved.
  • Discovery of small molecule human FPR1 receptor antagonists
    作者:John Unitt、Malbinder Fagura、Tim Phillips、Sarah King、Matthew Perry、Andrew Morley、Cathy MacDonald、Richard Weaver、Jadeen Christie、Simon Barber、Rukhsana Mohammed、Melanie Paul、Andrew Cook、Andrew Baxter
    DOI:10.1016/j.bmcl.2011.03.049
    日期:2011.5
    The identification of two novel series of formyl peptide receptor 1 (FPR1) antagonists are reported, represented by methionine benzimidazole 6 and diamide 7. Both series specifically inhibited the binding of labelled fMLF to hrFPR1 and selectively antagonized FPR1 function in human neutrophils, making them useful in vitro validation tools for the target. (C) 2011 Elsevier Ltd. All rights reserved.
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