N,N'-bis(2,3-dihydroxybenzoyl)-1,4-diaminopentane | 76218-84-3

• 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)-1,4-diaminopentane
• 英文别名: pentanochelin；N,N'-bis(2,3-dihydroxybenzoyl)-1,5-diaminopentane；N,N'-bis(2,3-dihydroxybenzoyl)-1,7-diazaheptane；1,5-bis[(2,3-dihydroxybenzoyl)amino]pentane；N,N'-Pentane-1,5-Diylbis(2,3-Dihydroxybenzamide)；N-[5-[(2,3-dihydroxybenzoyl)amino]pentyl]-2,3-dihydroxybenzamide
• CAS: 76218-84-3
• 化学式: C₁₉H₂₂N₂O₆
• 分子量: 374.393
• InChiKey: BRWLZTCRFJVZDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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)-1,4-diaminopentane 在 硫酸 作用下， 以79%的产率得到3-[5-[(2,3-Dihydroxy-5-sulfobenzoyl)amino]pentylcarbamoyl]-4,5-dihydroxybenzenesulfonic acid
  参考文献：
  名称：

  Sequestering agent for uranyl chelation: a new family of CAMS ligands

  摘要：

  The synthesis of new dipodal bis-sulfocatecholamide uranophiles is presented. Their binding abilities for uranyl cation were determined by UV spectro photometry in aqueous media under various pH conditions and further studied by H-1 NMR analysis of the resonance signal of both aromatic protons of the sulfocatecholamide groups. The results showed that the efficiency of these hydrosoluble chelating agents depends on the nature of the spacers. Each ligand shows a more or less pronounced affinity for uranium. The best receptor is the ligand CYCAMS 5d obtained as a mixture of cis/trans isomers, which achieves the best compromise between rigidity and steric hindrance. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.021
• 作为产物：
  描述：

  N,N'-di(2,3-dimethoxybenzoyl)-pentane-1,5-diamine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到N,N'-bis(2,3-dihydroxybenzoyl)-1,4-diaminopentane
  参考文献：
  名称：

  Sequestering agent for uranyl chelation: a new family of CAMS ligands

  摘要：

  The synthesis of new dipodal bis-sulfocatecholamide uranophiles is presented. Their binding abilities for uranyl cation were determined by UV spectro photometry in aqueous media under various pH conditions and further studied by H-1 NMR analysis of the resonance signal of both aromatic protons of the sulfocatecholamide groups. The results showed that the efficiency of these hydrosoluble chelating agents depends on the nature of the spacers. Each ligand shows a more or less pronounced affinity for uranium. The best receptor is the ligand CYCAMS 5d obtained as a mixture of cis/trans isomers, which achieves the best compromise between rigidity and steric hindrance. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.021

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。
• Complexation of Molybdenum by Siderophores:  Synthesis and Structure of the Double-Helical <i>cis</i>-Dioxomolybdenum(VI) Complex of a Bis(catecholamide) Siderophore Analogue
  作者：Anne-K. Duhme、Zbigniew Dauter、Robert C. Hider、Siegfried Pohl

  DOI：10.1021/ic9512183

  日期：1996.1.1
• Synthesis and evaluation of myxochelin analogues as antimetastatic agents
  作者：Satoshi Miyanaga、Hiroaki Sakurai、Ikuo Saiki、Hiroyasu Onaka、Yasuhiro Igarashi

  DOI：10.1016/j.bmc.2009.02.040

  日期：2009.4

  Myxochelin A (1) is an inhibitor of tumor cell invasion produced by the bacterium belonging to the genus Nonomuraea. In order to obtain more potent inhibitors, a series of myxochelin analogues [2 and (S)-3-17] were synthesized through the coupling of lysine or diaminoalkane derivatives and appropriately protected hydroxybenzoate, followed by modification of functional groups and deprotection. These compounds were evaluated for their inhibitory activity against invasion of murine colon 26-L5 carcinoma cells. Among the synthetic analogues tested, compound (S)-6 which possesses carbamoyl group at C-1 was found to be the most potent antiinvasive agent and is considered to be a promising lead molecule for the antimetastasis. Compound (S)-6 was also shown to inhibit gelatinase activities of MMP-2 and MMP-9 and in vivo lung metastasis in mice. (c) 2009 Elsevier Ltd. All rights reserved.
• Synthetic and Structural Studies of a Linear Bis-Catechol Amide, N,N'-Bis(2,3-dihydroxybenzoyl)-1,7-diazaheptane (5-LICAM), and Its Complexes with Ni2+ and Co2+: Utilization of a Polymer-Supported, Sulfonated Analog, 5-LICAMS, as a Biomimetic Ligand for Divalent Metal Ion Removal from Aqueous Solution
  作者：Song-Ping Huang、Katherine J. Franz、Marilyn M. Olmstead、Richard H. Fish

  DOI：10.1021/ic00115a007

  日期：1995.5

  The synthesis and structural characterization of the linear bis(catechol) amide ligand, N,N'-bis(2,3-dihydroxybenzoyl)-1 ,7-diazaheptane (5-LICAM, 1), was studied along with several metal complexes, namely, Ni2+ and Co2+. We were able to obtain a single-crystal X-ray analysis of a derivative of 1, the hemimethoxy ligand, 5-LICAM(OCH3)(2), 2, where partial demethylation of the fully methylated derivative of 1 was serendipitiously obtained in the presence of a deficiency of BBr3. The X-ray structure showed why we retained the methoxy group, during the partial demethylation reaction, in each catechol amide ring by the fact that a selective intramolecular hydrogen bond occurs between the one demethylated OH group in each catechol ring and the amide carbonyl in the adjacent position (C=O---HO, 1.67 Angstrom). Reaction of 1 with a Ni2+ salt provided the first structurally characterized square planar, linear bis-catechol amide, dianionic metal complex, with cesium as the counterion, Cs-2[5-LICAM-Ni]. 3DMF, 3, (Ni-O, 1.87 Angstrom, O-Ni-O, 87.9-92.5 degrees). It is also interesting to note that one of the cesium atoms was cis-bonded to the catechol oxygens in each ring (O2---Csl, O6-Csl=3.23 Angstrom, 3.03 Angstrom) and to the carbonyl oxygen of one of the three DMF solvent molecules (Csl-O=C, 3.13 Angstrom), while the other cesium atom was bonded to all three carbonyl oxygens of the DMF molecules in the structure (Cs2-O7, O8=3.13, 3.12 Angstrom). A Co2+ analogue of 3, Cs-2[5-LICAM-Co]. DMF, 4, provided a similar structure as ascertained by FT-IR, FAB/MS, and elemental analysis. In order to test the utilization of 1 in removing Ni2+ from aqueous solution for environmental inorganic applications, we synthesized the polymer pendant ligand version, PS-5-LICAM, bonded to modified 6% macroporous divinylbenzene-polystyrene beads (0.55 mmol/g), with an important modification of a sulfonate group on the catechol ring, PS-5-LICAMS IS, to impart hydrophilicity to the Ligand site. Indeed, we found that the PS-5-LICAMS ligand removed 0.35 mmol of Ni/g of polymer beads from aqueous solution at pH 2.5, but unfortunately, was not selective to Ni2+ in competition with other divalent metal ions. An in depth discussion of the X-ray structure of ligand 2 and that of the Ni complex, 3, will be presented.
• [EN] NOVEL FORMO-PHENOLIC RESINS, PROCESS FOR THE PREPARATION THEREOF, AND USE OF SAME IN THE EXTRACTION OF URANIUM FROM WATER<br/>[FR] NOUVELLES RESINES FORMO-PHENOLIQUES, LEUR PROCEDE DE PREPARATION, ET LEUR UTILISATION DANS L'EXTRACTION DE L'URANIUM DE L'EAU
  申请人：[fr]CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (CNRS)

  公开号：WO2022090242A1

  公开（公告）日：2022-05-05

  La présente invention a pour objet des résines formo-phénoliques, leur procédé de préparation, ainsi que leur utilisation dans l'extraction de l'uranium d'un échantillon aqueux. La présente Invention a également pour objet des nouvelles résines formo-phénoliques.