N,N'-bis(2,3-dihydroxybenzoyl)ethylenediamine | 71636-72-1

• 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-dihydroxybenzoyl)ethylenediamine
• 英文别名: N-[2-[(2,3-dihydroxybenzoyl)amino]ethyl]-2,3-dihydroxy-benzamide；N-[2-[(2,3-dihydroxybenzoyl)amino]ethyl]-2,3-dihydroxybenzamide
• CAS: 71636-72-1
• 化学式: C₁₆H₁₆N₂O₆
• 分子量: 332.313
• InChiKey: VPPFDDYSWNACAE-UHFFFAOYSA-N

物化性质

• 沸点：
  627.2±55.0 °C(Predicted)
• 密度：
  1.478±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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-dihydroxybenzoyl)ethylenediamine 在 硫酸 作用下， 以43%的产率得到N,N'-bis(2,3-dihydroxy-5-sulfobenzoyl)-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
• 作为产物：
  描述：

  地匹乙酯 在 吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N,N'-bis(2,3-dihydroxybenzoyl)ethylenediamine
  参考文献：
  名称：

  新化合物：N1，N8-双（2,3-二羟基苯甲酰基）亚精胺和类似物作为潜在的铁螯合药物。

  摘要：

  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。

  DOI：

  10.1002/jps.2600690836

文献信息

• [EN] IRON(III) AND GALLIUM(III) METAL ORGANIC POLYHEDRA, METHODS OF MAKING SAME, AND USES THEREOF<br/>[FR] POLYÈDRES ORGANIQUES MÉTALLIQUES DE FER(III) ET DE GALLIUM(III), LEURS PROCÉDÉS DE FABRICATION ET LEURS UTILISATIONS
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2020263761A1

  公开（公告）日：2020-12-30

  Compounds may have at least two structural units, which may be referred to as ligands. Each structural unit includes at least one spacer group and two or more donor groups. Compounds may have two or more iron(III) cations, one or more of which may be a high- spin iron(III) cation or high-spin iron(III) cations, two or more gallium(III) cations, or at least one iron(III) cation, one or more of which may be a high-spin iron(III) cation or high-spin iron(III) cations, and at least one gallium(III) cation, where the iron(III) cation(s) and/or the gallium(III) cation(s) coordinate to the donor groups. The compounds may be self-assembled cages. A composition may include one or more of the compound(s) and a pharmaceutically accepted carrier. Methods of imaging use one or more of the compound(s) and/or one or more of the composition(s).

  化合物可能至少有两个结构单元，可以称为配体。每个结构单元包括至少一个间隔基团和两个或更多供体基团。化合物可能具有两个或更多个铁（III）阳离子，其中一个或多个可能是高自旋铁（III）阳离子，两个或更多个镓（III）阳离子，或至少一个铁（III）阳离子，其中一个或多个可能是高自旋铁（III）阳离子，和至少一个镓（III）阳离子，其中铁（III）阳离子和/或镓（III）阳离子与供体基团配位。这些化合物可能是自组装笼状结构。一种组合物可能包括一个或多个这些化合物和一个药用可接受的载体。成像方法使用一个或多个这些化合物和/或一个或多个这些组合物。
• Selective Inhibition of Fe- versus Cu/Zn-Superoxide Dismutases by 2,3-Dihydroxybenzoic Acid Derivatives.
  作者：Laurent Soulère、Cécile Viodé、Jacques Périé、Pascal Hoffmann

  DOI：10.1248/cpb.50.578

  日期：——

  A series of catechol derivatives were synthesised and tested for their ability to inactivate the iron-containing superoxide dismutase (Fe-SOD) from Escherichia coli and the bovine erythrocytes Cu/Zn-SOD. Incubation of catechols with Fe- or Cu/Zn SODs resulted in a time-dependent loss of enzyme activity with highly selective inhibition for the iron-dependent enzyme. Catechol-induced inactivation of SODs was correlated with the auto-oxidation of the catechol compounds to their corresponding ortho-quinone derivatives, which was found to be non-dependent on the presence of enzymes. Mass electrospray experiments on catechol-incubated Fe-SOD provided evidence for the irreversible nature of the inhibition process, yielding to a complex mixture of modified proteins.

  一系列儿茶酚衍生物被合成并测试其抑制大肠杆菌中含铁超氧化物歧化酶（Fe-SOD）和牛红细胞铜/锌超氧化物歧化酶（Cu/Zn-SOD）的能力。儿茶酚与Fe-SOD或Cu/Zn-SOD的孵育导致酶活性的时间依赖性丧失，对依赖铁的酶具有高度选择性抑制作用。儿茶酚诱导的SOD失活与儿茶酚化合物自氧化为相应的邻醌衍生物相关，这一过程的发生并不依赖于酶的存在。对儿茶酚孵育的Fe-SOD进行的质谱电喷雾实验为抑制过程的不可逆性提供了证据，形成了一种修改蛋白的复杂混合物。
• 2,3-Dihydro-6,7-dihydroxy-1H-isoindol-1-one-Based HIV-1 Integrase Inhibitors
  作者：Xue Zhi Zhao、Elena A. Semenova、B. Christie Vu、Kasthuraiah Maddali、Christophe Marchand、Stephen H. Hughes、Yves Pommier、Terrence R. Burke

  DOI：10.1021/jm070715d

  日期：2008.1.1

  The bis-salicylhydrazides class of HIV-1 integrase (IN) inhibitors has been postulated to function by metal chelation. However, members of this series exhibit potent inhibition only when Mn2+ is used as cofactor. The current study found that bis-aroylhydrazides could acquire inhibitory potency in Mg2+ using dihydroxybenzoyl substituents as both the right and left components of the hydrazide moiety. Employing a 2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one ring system as a conformationally constrained 2,3-dihydroxybenzoyl equivalent provided good selectivity for IN-catalyzed strand transfer versus the 3'-processing reactions as well as antiviral efficacy in cells using HIV-1 based vectors.
• [EN] HYDRAZIDE, AMIDE, PHTHALIMIDE AND PHTHALHYDRAZIDE ANALOGS AS INHIBITORS OF RETROVIRAL INTEGRASE<br/>[FR] ANALOGUES D'HYDRAZIDE, D'AMIDE, DE PHTALIMIDE ET DE PHTALHYDRAZIDE EN TANT QU'INHIBITEURS DE L'INTÉGRASE RÉTROVIRALE
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2009026248A3

  公开（公告）日：2009-08-27
• 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.