N,N-bis(2,3-bis(hydroxy)benzoyl)diaminobutane | 71636-73-2

• 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-bis(hydroxy)benzoyl)diaminobutane
• 英文别名: N-{4-[(2,3-dihydroxyphenyl)formamido]butyl}-2,3-dihydroxybenzamide；butanochelin；N,N'-Butane-1,4-Diylbis(2,3-Dihydroxybenzamide)；N-[4-[(2,3-dihydroxybenzoyl)amino]butyl]-2,3-dihydroxybenzamide
• CAS: 71636-73-2
• 化学式: C₁₈H₂₀N₂O₆
• 分子量: 360.367
• InChiKey: FBRVRHJYPWFVCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  139
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N-bis(2,3-bis(hydroxy)benzoyl)diaminobutane 在 硫酸 作用下， 以42%的产率得到N,N'-bis(2,3-dihydroxy-5-sulfobenzoyl)-1,6-diazahexane
  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
• 作为产物：
  描述：

  N,N'-bis(2,3-dimethoxybenzoyl)-1,4-diaminobutane 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以14%的产率得到N,N-bis(2,3-bis(hydroxy)benzoyl)diaminobutane
  参考文献：
  名称：

  邻位邻苯二酚衍生物：分子内氢键途径对氯阴离子识别的影响

  摘要：

  本文报道了一系列含有两个邻苯二酚头基的氯阴离子受体，它们通过邻位链通过邻位连接。选择将间隔链连接至邻苯二酚单元的连接基团对受体的阴离子结合潜力有重大影响。能够与邻苯二酚OH基团形成稳定的六元分子内氢键合环的连接基团显着抑制了邻苯二酚单元与氯离子氢键合的能力。但是，在连接基团仅能够形成五元或七元分子内氢键合环的情况下，经由邻苯二酚OH基团通过氢键进行阴离子键合成为可能。该过程取决于溶剂。存在竞争性溶剂（例如DMSO- d 6）相对于简单的未官能化的邻苯二酚，破坏了分子内的氢键模式并增强了阴离子结合。最有效的受体是其中氢键连接基（-CH 2CONH-）与邻苯二酚单元距离最远，只能形成一个七元分子内氢键合环。在这种情况下，与两个简单的未官能化的邻苯二酚相比，包含两个邻苯二酚单元的受体是一种更有效的氯阴离子结合剂，表明两个头基与连接基团中的N-H基团协同作用并提高了其程度。阴离子结合。总之，本文提

  DOI：

  10.1021/jo0623989

文献信息

• New compounds: N-1, N8-bis(2, 3-dihydroxybenzoyl)spermidine and analogs as potential iron-chelating drugs
  作者：K.K. Bhargava、R.W. Grady、A. Cerami

  DOI：10.1002/jps.2600690836

  日期：1980.8

  N1,N8-bis(2,3-dihydroxybenzoyl)spermidine was synthesized and evaluated as an iron-chelating drug. Homologs were prepared and evaluated together with a series of N,N'-bis(2,3-dihydroxybenzoyl)-alpha,omega-diaminoalkanes. Analogous 2-hydroxbenzoyl compounds also were synthesized and evaluated.

  合成了N1，N8-双（2,3-二羟基苯甲酰基）亚精胺，并将其评价为铁螯合剂。制备同源物并与一系列N，N′-双（2，3-二羟基苯甲酰基）-α，ω-二氨基烷烃一起评估。还合成和评估了类似的2-羟基苯甲酰基化合物。
• Esters and lactones of phenolic amino carboxylic acids. Prodrugs for iron chelation
  作者：Colin G. Pitt、Y. Bao、J. Thompson、M. C. Wani、H. Rosenkrantz、J. Metterville

  DOI：10.1021/jm00157a020

  日期：1986.7

  The new iron chelator N,N'-bis(2-hydroxyphenyl)ethylenediamine-N,N'-diacetic acid (1), its dilactone 2, N,N'-bis(2-hydroxybenzyl)-2-hydroxypropylene-1,3-diamine-N,N'- diacetic acid (3), and its methyl ester lactone 4 and a series of esters of N,N'-bis(2-hydroxybenzyl)ethylenediamine-N,N'-diacetic acid (5) were prepared and their iron chelating efficacy and toxicity determined by using the hypertransfused

  新型铁螯合剂N，N'-双（2-羟基苯基）乙二胺-N，N'-二乙酸（1），双内酯2，N，N'-双（2-羟基苄基）-2-羟基丙烯-1， 3-二胺-N，N'-二乙酸（3）及其甲酯内酯4和N，N'-双（2-羟基苄基）乙二胺-N，N'-二乙酸的一系列酯（5）用超输血的铁超负荷小鼠模型制备了它们的铁螯合功效和毒性。将生物学活性与使用高输血大鼠获得的结果进行比较。酯化增强了口服铁螯合活性，但也增加了毒性。5的二异丙酯表现出最高的治疗指数。体外测量表明，在pH 7时酯水解的速率。在5 X 10（-4）M铁离子存在下，5的含量增加10（4）倍，这可能解释了酯和内酯作为前药的效用。筛选了其他十七种螯合剂，但没有腹膜内或口服活性。
• Interactions of a Periplasmic Binding Protein with a Tetradentate Siderophore Mimic
  作者：Daniel J. Raines、Olga V. Moroz、Keith S. Wilson、Anne-K. Duhme-Klair

  DOI：10.1002/anie.201300751

  日期：2013.4.22

  Iron‐bound structure: The ferric complex of a tetradentate siderophore mimic was synthesized and co‐crystallized with the periplasmic binding protein CeuE of Campylobacter jejuni. In addition to electrostatic and hydrogen‐bonding interactions between the binding pocket and the substrate, the structure showed direct coordination of two amino acid side chains to the FeIII center (orange, see figure)

  铁结合结构：合成了四齿铁载体模拟物的铁配合物，并与空肠弯曲杆菌周质结合蛋白CeuE共结晶。除了结合口袋和底物之间的静电和氢键相互作用外，该结构还显示出两个氨基酸侧链与Fe III中心的直接配位（橙色，见图）。
• 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.
• Loiseau; Trabelsi; Madaule, Arzneimittel-Forschung/Drug Research, 1996, vol. 46, # 11, p. 1095 - 1098
  作者：Loiseau、Trabelsi、Madaule、Bories、Wolf

  DOI：——

  日期：——