N-(2-hydroxy-1-naphthylidene)arginine | 162127-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-hydroxy-1-naphthylidene)arginine
• 英文别名: N-(2-hydroxy-1-naphthalidene)-L-arginine；(2S)-5-(diaminomethylideneamino)-2-[(2-hydroxynaphthalen-1-yl)methylideneamino]pentanoic acid
• CAS: 162127-27-7
• 化学式: C₁₇H₂₀N₄O₃
• 分子量: 328.371
• InChiKey: FJKUHWTYFZNGDA-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ammonium iron(II) sulfate hexahydrate 、 N-(2-hydroxy-1-naphthylidene)arginine 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis, physicochemical studies, embryos toxicity and DNA interaction of some new Iron(II) Schiff base amino acid complexes

  摘要：

  New Fe(II) Schiff base amino acid complexes derived from the condensation of o-hydroxynaphthaldehyde with L-alanine, L-phenylalanine, L-aspartic acid, L-histidine and L-arginine were synthesized and characterized by elemental analysis, IR, electronic spectra, and conductance measurements. The stoichiometry and the stability constants of the complexes were determined spectrophotometrically. The investigated Schiff bases exhibited tridentate coordination mode with the general formulae [Fe(HL)(2)]center dot nH(2)O for all amino acids except L-histidine. But in case of L-histidine, the ligand acts as tetradentate ([FeL(H2O)(2)]center dot 2H(2)O), where HL = mono anion and L = dianion of the ligand. The structure of the prepared complexes is suggested to be octahedral. The prepared complexes were tested for their toxicity on chick embryos and found to be safe until a concentration of 100 mu g/egg with full embryos formation. The interaction between CF-DNA and the investigated complexes were followed by spectrophotometry and viscosity measurements. It was found that, the prepared complexes bind to DNA via classical intercalative mode and showed a different DNA cleavage activity with the sequence: nhi > nari > nali > nasi > nphali. The thermodynamic Profile of the binding of nphali complex and CF-DNA was constructed by analyzing the experimental data of absorption titration and UV melting studies with the McGhee equation, van't Hoff's equation, and the Gibbs-Helmholtz equation. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2013.02.023
• 作为产物：
  描述：

  L-精氨酸 、 2-羟基-1-萘甲醛 以 甲醇 为溶剂， 反应 3.0h， 以70%的产率得到N-(2-hydroxy-1-naphthylidene)arginine
  参考文献：
  名称：

  新型N-（2-羟基-1-萘）-氨基酸（L-酪氨酸，L-精氨酸和L-赖氨酸）席夫碱及其锰（III）配合物的合成，表征和抗菌活性

  摘要：

  一系列新的锰（III）络合物Na [Mn（L 1）2 ] .3H 2 O，Na 3 [MnL 2（CH 3 COO）4 ] .2H 2 O，Na [Mn（L 3）2 ]。 2H 2 O和氨基酸席夫碱（H 2 L 1）；[N-（2-羟基-1-萘基）酪氨酸]，（H 2 L 2）；[N-（2-羟基-1-萘）精氨酸]，（H 2 L 3）；[N-（2-羟基-1-萘基）赖氨酸]是由2-羟基-1-萘醛和α-氨基酸（L-酪氨酸，L-精氨酸和L-赖氨酸）。使用元素分析，IR，UV-VIS，1 H-NMR光谱，磁化率测量和热重分析（TGA）鉴定化合物的结构。所有这些物质也已被检查了抗病原菌株的抗菌活性的金黄色葡萄球菌，嘘。dys。typ 7，单核细胞增生李斯特菌4b，大肠杆菌，S。typhi H，表皮葡萄球菌，Br。流产，黄体分枝杆菌，蜡状芽孢杆菌，恶臭假单胞菌和针对白色念珠菌的抗真菌活性。

  DOI：

  10.1080/15533174.2013.776604

文献信息

• Design, characterization, teratogenicity testing, antibacterial, antifungal and DNA interaction of few high spin Fe(II) Schiff base amino acid complexes
  作者：Laila H. Abdel-Rahman、Rafat M. El-Khatib、Lobna A.E. Nassr、Ahmed M. Abu-Dief、Fakhr El-Din Lashin

  DOI：10.1016/j.saa.2013.03.061

  日期：2013.7

  of the complexes were determined spectrophotometrically. Correlation of all spectroscopic data suggested that Schiff bases ligands exhibited tridentate with ONO sites coordinating to the metal ions via protonated phenolic-OH, azomethine-N and carboxylate-O with the general formulae [Fe(HL)2]·nH2O. But in case of l-histidine, the ligand acts as tetradentate via deprotonated phenolic-OH, azomethine-N,

  在这项研究中，合成了由邻羟基萘甲醛与1-丙氨酸，1-苯丙氨酸，1-天冬氨酸，1-组氨酸和1-精氨酸缩合而成的新的Fe（II）席夫碱氨基酸螯合物。热重分析，摩尔电导，红外，电子，质谱和磁矩测量。分光光度法测定了配合物的化学计量和稳定性常数。所有光谱数据的相关性表明，席夫碱配体表现出三齿形，其ONO位点通过具有通式[Fe（HL）2 ]·的质子化酚醛-OH，偶氮甲碱-N和羧酸酯-O与金属离子配位。Ñ ħ 2 O.但是，在的情况下，升-组氨酸，所述配体充当通过去质子化的酚OH，偶氮甲碱-N，羧酸盐的O和N的咪唑环（[FEL（H四齿2 O）2 ]·2H 2 ö ），其中HL =配体的单阴离子和L =二价阴离子。建议制备的配合物的结构为八面体。测试了制备的复合物的致畸性在雏鸡胚胎上使用，直到浓度达到100μg/蛋且完整的胚胎形成时才是安全的。此外，通过分光光度法和粘度测量来跟踪CT-DNA与所研究的复
• Supramolecular assembly of a new series of copper-l-arginine Schiff bases
  作者：Siu Yee New、Yude Thio、Lip Lin Koh、T. S. Andy Hor、Feng Xue

  DOI：10.1039/c0ce00444h

  日期：——

  A series of copper-L-arginine complexes has been synthesized and characterized by spectroscopic and single-crystal X-ray diffraction analyses. The L-arginine Schiff bases invariably show [ONO] tridentate coordination on a mononuclear Cu(II) sphere. [Cu(RNap)(OAc)]·2H2O, 1 (RNap = N-(2-hydroxy-1-naphthalidene) L-arginine), obtained from Cu(OAc)2·2H2O and HRNap, gives two stereochemically different molecules in the crystal unit cell, with each of them showing different acetate binding modes. It exhibits a channel structure with disordered water molecules filling the cavity. Complexation of N-(2-hydroxy-5-nitro-1-salicylidene) L-arginine (HRNO2) with Cu(ClO4)2·6H2O yields the intriguing triclinic crystal structure of 2. Its unit cell consists of a neutral molecule [Cu(RNO2)Cl(H2O)], an ion pair [Cu(RNO2)(H2O)2]ClO4 and three water molecules of crystallization. Complexation of HRMe (RMe = N-(2-hydroxy-5-methyl-1-salicylidene) with Cu(OAc)2·2H2O gives [Cu(RMe)(OAc)]·5H2O, 3, whose crystal packing shows a zeolite-like network with a water cluster residing in the hydrophilic channel, thus facilitating the hydrogen bonding interaction.

  一系列铜-L-精氨酸复合物已经合成，并通过光谱和单晶X射线衍射分析对其进行了表征。L-精氨酸席夫碱在单核Cu(II)球体上总是表现出[ONO]三叉配位。从Cu(OAc)2·2 和HRNap得到的[Cu(RNap)(OAc)]·2 , 1（RNap = N-(2-羟基-1-萘亚甲基) L-精氨酸）在晶胞中给出两个立体化学不同的分子，每个分子表现出不同的乙酸盐结合模式。它表现出通道结构，无序的水分子填充在空腔中。N-(2-羟基-5-硝基-1-水杨亚甲基) L-精氨酸（HRNO2）与Cu(ClO4)2·6 的络合产生了有趣的2三斜晶结构。其晶胞由中性分子[Cu(RNO2)Cl(H2O)]、离子对[Cu(RNO2)( )2] 和三个结晶水分子组成。HRMe（RMe = N-(2-羟基-5-甲基-1-水杨亚甲基)）与Cu(OAc)2·2 的络合产生了[Cu(RMe)(OAc)]