5-chloro-3-[(2,6-difluorophenyl)methyl]-1H-benzimidazol-2-one | 852690-06-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-chloro-3-[(2,6-difluorophenyl)methyl]-1H-benzimidazol-2-one
• CAS: 852690-06-3
• 化学式: C₁₄H₉ClF₂N₂O
• 分子量: 294.688
• InChiKey: YMOMBCSJYZNOLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-chloro-3-[(2,6-difluorophenyl)methyl]-1H-benzimidazol-2-one 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以84%的产率得到1-Acetyl-5-chloro-3-[(2,6-difluorophenyl)methyl]benzimidazol-2-one
  参考文献：
  名称：

  新型的N1取代的1,3-二氢-2H-苯并咪唑-2-酮类作为有效的非核苷类逆转录酶抑制剂。

  摘要：

  合成了多个N（1）-取代的1,3-二氢-2H-苯并咪唑-2-酮，并作为抗HIV药物进行了评估。它们中的一些被证明在纳摩尔浓度下作为抑制细胞毒性低的有效非核苷HIV-1 RT抑制剂（NNRTIs）能有效抑制HIV-1复制。SAR研究突出表明，苯并咪唑酮部分的N（1）和苯环上的取代基的性质显着影响此类有效的抗逆转录病毒药物的抗HIV活性。

  DOI：

  10.1016/j.bmc.2008.06.012
• 作为产物：
  描述：

  5-chloro-1-(2,6-difluorobenzyl)-2-nitroaniline 在 盐酸 、 锌 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 5.0h， 生成 5-chloro-3-[(2,6-difluorophenyl)methyl]-1H-benzimidazol-2-one
  参考文献：
  名称：

  Computational Strategies in Discovering Novel Non-nucleoside Inhibitors of HIV-1 RT

  摘要：

  A three-dimensional common feature pharmacophore model was developed using the X-ray structure of RT/non-nucleoside inhibitor (NNRTI) complexes. Starting from the pharmacophore hypothesis and the structure of the lead compound TBZ, new NNRTIs were designed and synthesized, having the benzimidazol-2-one system as a scaffold. Docking experiments showed that these molecules docked in a position and orientation similar to that of known inhibitors. Biological testing confirmed that our strategy was successful in searching for new leads as NNRTIs.

  DOI：

  10.1021/jm049279a

文献信息

• Novel N1-substituted 1,3-dihydro-2H-benzimidazol-2-ones as potent non-nucleoside reverse transcriptase inhibitors
  作者：Anna-Maria Monforte、Angela Rao、Patrizia Logoteta、Stefania Ferro、Laura De Luca、Maria Letizia Barreca、Nunzio Iraci、Giovanni Maga、Erik De Clercq、Christophe Pannecouque、Alba Chimirri

  DOI：10.1016/j.bmc.2008.06.012

  日期：2008.8

  synthesized and evaluated as anti-HIV agents. Some of them proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentration as potent non-nucleoside HIV-1 RT inhibitors (NNRTIs) with low cytotoxicity. SAR studies highlighted that the nature of the substituents at N(1) and on the benzene ring of benzimidazolone moiety significantly influenced the anti-HIV activity of this class

  合成了多个N（1）-取代的1,3-二氢-2H-苯并咪唑-2-酮，并作为抗HIV药物进行了评估。它们中的一些被证明在纳摩尔浓度下作为抑制细胞毒性低的有效非核苷HIV-1 RT抑制剂（NNRTIs）能有效抑制HIV-1复制。SAR研究突出表明，苯并咪唑酮部分的N（1）和苯环上的取代基的性质显着影响此类有效的抗逆转录病毒药物的抗HIV活性。
• Computational Strategies in Discovering Novel Non-nucleoside Inhibitors of HIV-1 RT
  作者：Maria Letizia Barreca、Angela Rao、Laura De Luca、Maria Zappalà、Anna-Maria Monforte、Giovanni Maga、Christophe Pannecouque、Jan Balzarini、Erik De Clercq、Alba Chimirri、Pietro Monforte

  DOI：10.1021/jm049279a

  日期：2005.5.1

  A three-dimensional common feature pharmacophore model was developed using the X-ray structure of RT/non-nucleoside inhibitor (NNRTI) complexes. Starting from the pharmacophore hypothesis and the structure of the lead compound TBZ, new NNRTIs were designed and synthesized, having the benzimidazol-2-one system as a scaffold. Docking experiments showed that these molecules docked in a position and orientation similar to that of known inhibitors. Biological testing confirmed that our strategy was successful in searching for new leads as NNRTIs.