N-(2-hydroxy-1-naphthylidene)-L-phenylalanine | 760926-43-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2-hydroxy-1-naphthylidene)-L-phenylalanine
• 英文别名: (2S)-2-[(2-hydroxynaphthalen-1-yl)methylideneamino]-3-phenylpropanoic acid
• CAS: 760926-43-0
• 化学式: C₂₀H₁₇NO₃
• 分子量: 319.36
• InChiKey: HTXDCKPVAKOCMY-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-1-naphthylidene)-L-phenylalanine 、 ferrous ammonium sulfate hexahydrate 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以83%的产率得到
  参考文献：
  名称：

  几种高自旋Fe（II）Schiff碱氨基酸复合物的设计，表征，致畸性测试，抗菌，抗真菌和DNA相互作用

  摘要：

  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

  DOI：

  10.1016/j.saa.2013.03.061
• 作为产物：
  描述：

  L-苯丙氨酸 、 2-羟基-1-萘甲醛 以 甲醇 为溶剂， 反应 0.5h， 生成 N-(2-hydroxy-1-naphthylidene)-L-phenylalanine
  参考文献：
  名称：

  基于 O,N,O-三齿席夫碱的新型铜 (II) 配合物的合成、固态结构和脲酶抑制活性

  摘要：

  摘要 合成了六种与O,N,O-三齿席夫碱二价阴离子配位的新型铜(II)配合物并对其进行了结构表征。1-6 的固态结构包含四坐标单核铜 (II) 单元，具有略微扭曲的方形平面几何形状。来自 d-酪氨酸的复合物 1 和 4 具有无限的一维右旋螺旋链，而衍生自 l-酪氨酸的复合物 5 具有无限的一维左旋螺旋链。已经研究了 1-6 对 jack bean 脲酶的抑制作用，并且已经观察到这些铜 (II) 复合物的有效抑制活性，IC50 范围为 2.15 ± 0.11-32.12 ± 0.65 μM。使用 DOCK 程序进行对接分析，将 4 定位到长豆豆脲酶活性位点中，以确定可能的结合构象。

  DOI：

  10.1080/00958972.2016.1206199

文献信息

• Tautomerism in N-(2-hydroxy-1-naphthylidene)amino acids and the search for an answer to the difficult question about where the proton belongs
  作者：Gisela Warncke、Sabine Fels、Erica Brendler、Uwe Böhme

  DOI：10.1016/j.molstruc.2016.03.040

  日期：2016.8

  spectroscopic methods, elemental analyses, and values of optical rotation. Compound 1 undergoes a solid state order-disorder phase transition at 231 K. The X-ray structures of the high and low temperature phase of 1 have been determined. Single crystal X-ray structures of 2 and 3 have been determined as well. The tautomerism of N-(2-hydroxy-1-naphthylidene)amino acid derivatives is discussed controversial

  摘要 N-(2-羟基-1-亚萘基)-l-缬氨酸1、N-(2-羟基-1-亚萘基)-l-苯丙氨酸2和N-(2-羟基-1-亚萘基)-l-苏氨酸 3 被制备并用光谱方法、元素分析和旋光度值表征。化合物 1 在 231 K 下经历固态有序-无序相变。 1 的高温和低温相的 X 射线结构已确定。2 和 3 的单晶 X 射线结构也已确定。N-(2-hydroxy-1-naphthylidene) 氨基酸衍生物的互变异构现象在文献中存在争议。键长统计分析表明，所有三种化合物均以固态的酮胺形式均匀存在。量子化学计算，核磁共振，
• Synthesis, physicochemical studies, embryos toxicity and DNA interaction of some new Iron(II) Schiff base amino acid complexes
  作者：Laila H. Abdel-Rahman、Rafat M. El-Khatib、Lobna A.E. Nassr、Ahmed M. Abu-Dief

  DOI：10.1016/j.molstruc.2013.02.023

  日期：2013.5

  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.
• Synthesis and structural characterisation of new Re(III) complexes using aldimines of α-amino acids as coligands
  作者：Sucharita Basak、Amrita Mondal、Deepak Chopra、Kajal Krishna Rajak

  DOI：10.1016/j.poly.2007.03.036

  日期：2007.8

  Complexes of the general formula [Re-III(L)CI(PPh3)2] have been synthesised by reacting H2L and [ReOCl3(PPh3)(2)] in ethanol. Here H2L represents imines of alpha-amino acids (glycine, L-alanine, L-valine, L-phenylalanine) derived from salicylaldehyde and naphthaldehyde. The crystal structure of one complex has been determined. The complexes are monomiclear, paramagnetic and display paramagnetic H-1 NMR in CDCl3 solution. Their spectral and redox properties are scrutinised. (c) 2007 Elsevier Ltd. All rights reserved.