4-chloro-N-furan-2-ylmethyl-N-(6-methyl-2-oxo-1,2-dihydro-quinolin-3-ylmethyl)-3-piperidin-1-yl-benzamide | 1207642-84-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-chloro-N-furan-2-ylmethyl-N-(6-methyl-2-oxo-1,2-dihydro-quinolin-3-ylmethyl)-3-piperidin-1-yl-benzamide
• 英文别名: 4-chloro-N-(2-furylmethyl)-N-[(6-methyl-2-oxo-1H-quinolin-3-yl)methyl]-3-(1-piperidyl)benzamide；4-chloro-N-(furan-2-ylmethyl)-N-[(6-methyl-2-oxo-1H-quinolin-3-yl)methyl]-3-piperidin-1-ylbenzamide
• CAS: 1207642-84-9
• 化学式: C₂₈H₂₈ClN₃O₃
• 分子量: 490.002
• InChiKey: YTROPQCXOUNPAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-chloro-3-piperidin-1-yl-benzoic acid 、 3-{[(furan-2-ylmethyl)-amino]-methyl}-6-methyl-1H-quinolin-2-one 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 以48%的产率得到4-chloro-N-furan-2-ylmethyl-N-(6-methyl-2-oxo-1,2-dihydro-quinolin-3-ylmethyl)-3-piperidin-1-yl-benzamide
  参考文献：
  名称：

  Virtual screening based identification of novel small-molecule inhibitors targeted to the HIV-1 capsid

  摘要：

  The hydrophobic cavity of the C-terminal domain (CTD) of HIV-1 capsid has been recently validated as potential target for antiviral drugs by peptide-based inhibitors; however, there is no report yet of any small molecule compounds that target this hydrophobic cavity. In order to fill this gap and discover new classes of ant-HIV-1 inhibitors, we undertook a docking-based virtual screening and subsequent analog search, and medicinal chemistry approaches to identify small molecule inhibitors against this target. This article reports for the first time, to the best of our knowledge, identification of diverse classes of inhibitors that efficiently inhibited the formation of mature-like viral particles verified under electron microscope (EM) and showed potential as anti-HIV-1 agents in a viral infectivity assay against a wide range of laboratory-adapted as well as primary isolates in MT-2 cells and PBMC. In addition, the virions produced after the HIV-1 infected cells were treated with two of the most active compounds showed drastically reduced infectivity confirming the potential of these compounds as anti-HIV-1 agents. We have derived a comprehensive SAR from the antiviral data. The SAR analyses will be useful in further optimizing the leads to potential anti-HIV-1 agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.045

文献信息

• Small Molecule Inhibitors of Retroviral Assembly & Maturation
  申请人：New York Blood Center

  公开号：EP2335779A1

  公开（公告）日：2011-06-22

  Chemical compounds that disrupt retroviral assembly and maturation are presented herein. More particularly, this disclosure provides small molecule compounds that disrupt the formation and maturation of virus particles and methods of using such small molecules to treat HIV-1 infection.

  本文介绍了能破坏逆转录病毒组装和成熟的化学化合物。更具体地说，本公开提供了能破坏病毒颗粒的形成和成熟的小分子化合物，以及用这种小分子化合物治疗 HIV-1 感染的方法。
• Small Molecule Inhibitors of Retroviral Assembly and Maturation
  申请人：Debnath Asim Kumar

  公开号：US20100035912A1

  公开（公告）日：2010-02-11

  Chemical compounds that disrupt retroviral assembly and maturation are presented herein. More particularly, this disclosure provides small molecule compounds that disrupt the formation and maturation of virus particles and methods of using such small molecules to treat HIV-1 infection.
• US8299093B2
  申请人：——

  公开号：US8299093B2

  公开（公告）日：2012-10-30
• US8546439B2
  申请人：——

  公开号：US8546439B2

  公开（公告）日：2013-10-01
• [EN] SMALL MOLECULE INHIBITORS OF RETROVIRAL ASSEMBLY AND MATURATION<br/>[FR] INHIBITEURS À PETITE MOLÉCULE D'ASSEMBLAGE ET DE MATURATION RÉTROVIRAUX
  申请人：NEW YORK BLOOD CT INC

  公开号：WO2010017355A2

  公开（公告）日：2010-02-11

  Chemical compounds that disrupt retroviral assembly and maturation are presented herein. More particularly, this disclosure provides small molecule compounds that disrupt the formation and maturation of virus particles and methods of using such small molecules to treat HIV-1 infection.