N,N'-bis(2,3-dimethoxybenzoyl)-1,4-diazabutane | 73630-94-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis(2,3-dimethoxybenzoyl)-1,4-diazabutane
• 英文别名: N,N'-di(2,3-dimethoxybenzoyl)-ethylenediamine；N-[2-[(2,3-dimethoxybenzoyl)amino]ethyl]-2,3-dimethoxybenzamide
• CAS: 73630-94-1
• 化学式: C₂₀H₂₄N₂O₆
• 分子量: 388.42
• InChiKey: BKNFPOYEMCRTQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2,3-dimethoxybenzoyl)-1,4-diazabutane 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到N,N'-bis(2,3-dihydroxybenzoyl)ethylenediamine
  参考文献：
  名称：

  Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors

  摘要：

  Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV.Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties.The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.033
• 作为产物：
  描述：

  2,3-二甲氧基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 23.0h， 生成 N,N'-bis(2,3-dimethoxybenzoyl)-1,4-diazabutane
  参考文献：
  名称：

  Specific sequestering agents for the actinides. 3. Polycatecholate ligands derived from 2,3-dihydroxy-5-sulfobenzoyl conjugates of diaza- and tetraazaalkanes

  摘要：

  DOI：

  10.1021/ja00527a026

文献信息

• High Yield Selective Acylation of Polyamines:  Proton as Protecting Group
  作者：Asmik Oganesyan、Iris A. Cruz、Roberto B. Amador、Nohemy A. Sorto、Jose Lozano、Carlos E. Godinez、Jaime Anguiano、Heather Pace、Ghiwa Sabih、Carlos G. Gutierrez

  DOI：10.1021/ol702206d

  日期：2007.11.1

  An advance in the selective acylation of polyamines having identical or similar amine functions is reported. While nucleophilicity differences between the various amine functions are slight, the corresponding conjugate acids exhibit pK(a) values over a significant range. We have used proton as polyamine protecting group: the monoamine resulting from single deprotonation of a polyammonium compound has allowed for high yields of selective acylation.
• Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors
  作者：Eva Rivero-Buceta、Paula Carrero、Elisa G. Doyagüez、Andrés Madrona、Ernesto Quesada、María José Camarasa、María Jesús Peréz-Pérez、Pieter Leyssen、Jan Paeshuyse、Jan Balzarini、Johan Neyts、Ana San-Félix

  DOI：10.1016/j.ejmech.2015.01.033

  日期：2015.3

  Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV.Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties.The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Specific sequestering agents for the actinides. 3. Polycatecholate ligands derived from 2,3-dihydroxy-5-sulfobenzoyl conjugates of diaza- and tetraazaalkanes
  作者：Frederick L. Weitl、Kenneth N. Raymond

  DOI：10.1021/ja00527a026

  日期：1980.3