N-(3-chlorophenyl)-4-(1,3-dioxoisoindolin-2-yl)benzenesulphonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-(3-chlorophenyl)-4-(1,3-dioxoisoindolin-2-yl)benzenesulphonamide
• 英文别名: N-(3-chlorophenyl)-4-(1,3-dioxoisoindolin-2-yl)benzenesulphonamide (11)；N-(3-chlorophenyl)-4-(1,3-dioxoisoindol-2-yl)benzenesulfonamide
• 化学式: C₂₀H₁₃ClN₂O₄S
• 分子量: 412.853
• InChiKey: NEIMGUMPOQWCKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-苯基邻苯二甲酰亚胺 在 吡啶 、 氯磺酸 、 五氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 N-(3-chlorophenyl)-4-(1,3-dioxoisoindolin-2-yl)benzenesulphonamide
  参考文献：
  名称：

  Synthesis and molecular modelling studies of novel sulphonamide derivatives as dengue virus 2 protease inhibitors

  摘要：

  Development of antivirals for dengue is now based on rational approach targeting the enzymes involved in its life cycle. Among the targets available for inhibition of dengue virus, non-structural protein NS2B-NS3 protease is considered as a promising target for the development of anti-dengue agents. In the current study we have synthesized a series of 4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)benzene-1-sulphonamide derivatives and screened for DENV2 protease activity. Compounds 16 and 19 showed IC50 of DENV2 Protease activity with 48.2 and 121.9 mu M respectively. Molecular docking and molecular dynamic simulation studies were carried out to know the binding mode responsible for the activity. MD simulations revealed that, NS2B/NS3 protease was more stable when it binds with the active compound. Structure optimization of the lead compounds 16 and 19 and their co-crystallization studies are underway. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.07.005

文献信息

• Synthesis and molecular modelling studies of novel sulphonamide derivatives as dengue virus 2 protease inhibitors
  作者：Ajay Kumar Timiri、Subasri Selvarasu、Manish Kesherwani、Vishwanathan Vijayan、Barij Nayan Sinha、Velmurugan Devadasan、Venkatesan Jayaprakash

  DOI：10.1016/j.bioorg.2015.07.005

  日期：2015.10

  Development of antivirals for dengue is now based on rational approach targeting the enzymes involved in its life cycle. Among the targets available for inhibition of dengue virus, non-structural protein NS2B-NS3 protease is considered as a promising target for the development of anti-dengue agents. In the current study we have synthesized a series of 4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)benzene-1-sulphonamide derivatives and screened for DENV2 protease activity. Compounds 16 and 19 showed IC50 of DENV2 Protease activity with 48.2 and 121.9 mu M respectively. Molecular docking and molecular dynamic simulation studies were carried out to know the binding mode responsible for the activity. MD simulations revealed that, NS2B/NS3 protease was more stable when it binds with the active compound. Structure optimization of the lead compounds 16 and 19 and their co-crystallization studies are underway. (C) 2015 Elsevier Inc. All rights reserved.