1-[(2,6-二氟苯基)甲基]-2-苯基苯并咪唑 | 199594-73-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 1-[(2,6-二氟苯基)甲基]-2-苯基苯并咪唑
• 英文名称: 1-(2,6-difluorobenzyl)-2-phenyl-1H-benzimidazole
• 英文别名: 1-(2,6-difluorobenzyl)-2-phenylbenzimidazole；1H-Benzimidazole, 1-((2,6-difluorophenyl)methyl)-2-phenyl-；1-[(2,6-difluorophenyl)methyl]-2-phenylbenzimidazole
• CAS: 199594-73-5
• 化学式: C₂₀H₁₄F₂N₂
• 分子量: 320.341
• InChiKey: KBOHDHODCNDQPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(2,6-difluorobenzyl)benzene-1,2-diamine 、 苯甲醛 在 Pd-MgO 、 氧气 作用下， 以 2,3,4-三氟甲苯 为溶剂， 以0.282 g的产率得到1-[(2,6-二氟苯基)甲基]-2-苯基苯并咪唑
  参考文献：
  名称：

  单-和双官能固体催化剂通过一锅多步法合成苯并咪唑的新途径

  摘要：

  已开发出涉及新型环境友好催化程序的一锅多步反应，用于合成苯并咪唑。具有生物学和药学意义的苯并咪唑衍生物已经通过一锅四步法用含有碱性和氧化位点的固体催化剂制备。这四个步骤涉及：（a）醇的氧化；（b）与邻苯二胺形成的醛的环缩合；（c）碳氮键的氧化；（d）N烷基化反应。通过合成具有抗病毒活性的1,2-二取代的苯并咪唑衍生物可以说明这一过程。

  DOI：

  10.1016/j.tet.2009.11.048

文献信息

• Substituted benzimidazoles, and methods of use thereof, for the inhibition of HIV reverse transcription and for the treatment of HIV infection
  申请人：The United States of America as represented by the Department of Health and Human Services

  公开号：US06369235B1

  公开（公告）日：2002-04-09

  The present invention provides compositions and methods for the treatment of HIV infection. In particular, the present invention provides non-nucleoside inhibitors of reverse transcriptase (RT), as well as methods to treat HIV infection using these non-nucleoside inhibitors of RT. In preferred embodiments, the present invention provides a novel class of substituted benzimidazoles, effective in the inhibition of human immunodeficiency virus (HIV) RT.

  本发明提供了用于治疗HIV感染的组合物和方法。具体来说，本发明提供了非核苷类逆转录酶（RT）抑制剂，以及使用这些非核苷类RT抑制剂治疗HIV感染的方法。在优选实施例中，本发明提供了一类新型的取代苯并咪唑化合物，对人类免疫缺陷病毒（HIV）RT的抑制效果显著。
• Synthesis and Biological Activity of Novel Nonnucleoside Inhibitors of HIV-1 Reverse Transcriptase. 2-Aryl-Substituted Benzimidazoles
  作者：Thomas Roth、Marshall L. Morningstar、Paul L. Boyer、Stephen H. Hughes、Robert W. Buckheit,、Christopher J. Michejda

  DOI：10.1021/jm970096g

  日期：1997.12.1

  nonnucleoside inhibitors of human immunodeficiency virus type-1 (HIV-1) reverse transcriptase (RT) active against the drug-induced mutations in RT continues to be a very important goal of AIDS research. We used a known inhibitor of HIV-1 RT, 1-(2,6-difluorophenyl)-1H,3H-thiazolo[3,4-alpha]benzimidazole (TZB), as the lead structure for drug design with the objective of making more potent inhibitors against

  对抗药物诱导的RT突变的新型人类免疫缺陷病毒1型（HIV-1）逆转录酶（RT）的非核苷抑制剂的开发仍然是艾滋病研究的一个重要目标。我们使用已知的HIV-1 RT抑制剂1-（2,6-二氟苯基）-1H，3H-噻唑并[3,4-α]苯并咪唑（TZB）作为药物设计的主要结构，目的在于制备针对野生型（WT）和变异RT的更有效抑制剂。合成了一系列结构上相关的1,2-取代的苯并咪唑，并评估了它们抑制HIV-1 WT RT体外聚合的能力。对一系列化合物进行了结构活性研究，以确定在N1和C2位置取代苯并咪唑环的最佳基团。最好的抑制剂1-（2,6-二氟苄基）-2-（2，6-二氟苯基）-4-甲基苯并咪唑（35）在体外酶分析中对HIV-1 WT RT的IC50 = 200 nM。利用HIV感染的MT-4细胞进行的细胞保护分析显示，35种具有对野生型病毒的强抗病毒活性（EC50 = 440 nM），同时对许多对非核苷
• [EN] SUBSTITUTED BENZIMIDAZOLES AS NON-NUCLEOSIDE INHIBITORS OF REVERSE TRANSCRIPTASE<br/>[FR] BENZIMIDAZOLES SUBSTITUES EN TANT QU'INHIBITEURS NON NUCLEOSIDIQUES DE LA TRANSCRIPTASE INVERSE
  申请人：US HEALTH

  公开号：WO2001014343A1

  公开（公告）日：2001-03-01

  Benzimidazole derivatives substituted in position 2 by a 2,6 difluorophenyl and/or in position 1 by a 2,6-difluorobenzyl group are HIV-1 reverse transcriptase inhibitors useful in treatment of HIV infections.

  2-位置被2,6-二氟苯基和/或1-位置被2,6-二氟苄基取代的苯并咪唑衍生物是HIV-1反转录酶抑制剂，可用于治疗HIV感染。
• Substituted benzimidazoles as non-nucleoside inhibitors of reverse transcriptase
  申请人：——

  公开号：US20030191160A1

  公开（公告）日：2003-10-09

  The present invention provides compositions and methods for the treatment of HIV infection. In particular, the present invention provides non-nucleoside inhibitors of reverse transcriptase (RT), as well as methods to treat HIV infection using these non-nucleoside inhibitors of RT. In preferred embodiments, the present invention provides a novel class of substituted benzimidazoles, effective in the inhibition of human immunodeficiency virus (HIV) RT.

  本发明提供了治疗HIV感染的组合物和方法。特别是，本发明提供了反转录酶（RT）非核苷类抑制剂，以及使用这些非核苷类RT抑制剂治疗HIV感染的方法。在优选实施例中，本发明提供了一类新型的取代苯并咪唑，能够有效抑制人类免疫缺陷病毒（HIV）RT。
• Manganese oxide catalyzed synthesis of anti-HIV N-substituted benzimidazoles via a one-pot multistep process
  作者：Xiuru Bi、Xu Meng、Gexin Chen、Baohua Chen、Peiqing Zhao

  DOI：10.1016/j.catcom.2018.07.020

  日期：2018.11

  1, 2-Disubstituted benzimidazoles are drug discovery targets and play an important role in many areas. Herein, non-noble-metal alpha-MnO2 prepared using urea as the additive was found to be an efficient catalyst for the synthesis of antiviral 1,2-disubstituted benzimidazoles via one-pot multistep reactions using dimethyl carbonate and air as green solvent and oxidant, respectively. The catalytic system could tolerate 1, 2-diol or alcohols as raw via cascade oxidation/cyclization/alkylation to realize the desired products in moderate to good yields. The catalyst was characterized by ICP-AES, XRD, BET, SEM, TEM and XPS, which indicates that the surface oxygen species seriously affected the catalytic performance. And the leaching of Na/K ions in tunnels of the catalyst caused loss of catalytic activity of retrieved alpha-MnO2.