2-hydroxy-N-[(2-oxo-1H-quinolin-3-yl)methylideneamino]benzamide | 880071-97-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-hydroxy-N-[(2-oxo-1H-quinolin-3-yl)methylideneamino]benzamide
• CAS: 880071-97-6
• 化学式: C₁₇H₁₃N₃O₃
• 分子量: 307.309
• InChiKey: DAHPWFATRAVZHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲醇 、 copper(II) nitrate trihydrate 、 2-hydroxy-N-[(2-oxo-1H-quinolin-3-yl)methylideneamino]benzamide 以 甲醇 为溶剂， 以82%的产率得到[Cu(2-oxo-1,2-dihydroquinoline-3-carbaldehyde(2'-hydroxybenzoyl)hydrazone)(MeOH)2](NO3)
  参考文献：
  名称：

  DNA binding, protein interaction, radical scavenging and cytotoxic activity of 2-oxo-1,2-dihydroquinoline-3-carbaldehyde(2′-hydroxybenzoyl)hydrazone and its Cu(II) complexes: A structure activity relationship study

  摘要：

  Two new copper(II) complexes have been synthesized by reacting 2-oxo-1,2-dihydroquinoline-3-carbaldehyde( 2'-hydroxybenzoyl) hydrazone (H2L) (1) with CuCl2 center dot 2H(2)O or Cu(NO3)(2)center dot 3H(2)O, in order to obtain a clear picture on the role of counter ion in the biological properties of the complexes so obtained. Single-crystal X-ray diffraction studies revealed that both the complexes [CuCl(HL)(H2O)]center dot CH3OH (2) and [Cu(HL)(CH3OH)(2)]NO3 (3) have square pyramidal geometry with the ligand coordinating through uninegative tridentate ONO fashion. The UV-Vis and fluorescence spectroscopy experimental evidences strongly suggested that the ligand and the two Cu(II) complexes could interact with calf thymus DNA (CT-DNA) through intercalation. The interactions of the compounds to bovine serum albumin (BSA) were investigated by UV-Vis, fluorescence and synchronous fluorescence spectra. The results indicated that all the three compounds could quench the intrinsic fluorescence of BSA in a static quenching way. Investigations of antioxidative properties showed that all the compounds have strong radical scavenging properties. Cytotoxic studies showed that the two copper(II) complexes exhibited effective cytotoxic activity against HeLa cancer cells. Overall, the complex 3 has exhibited better biological activity than that of the complex 2 and the ligand. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.12.038
• 作为产物：
  描述：

  水杨酰肼 、 1,2-二氢-2-氧代喹啉-3-甲醛 以 乙醇 为溶剂， 以80%的产率得到2-hydroxy-N-[(2-oxo-1H-quinolin-3-yl)methylideneamino]benzamide
  参考文献：
  名称：

  Synthesis, characterization, antibiogram and DNA binding studies of novel Co(II), Ni(II), Cu(II), and Zn(II) complexes of Schiff base ligands with quinoline core

  摘要：

  A series of Co(II), Ni(II), Cu(II), and Zn(II) complexes of Schiff base ligands (LH3)-H-1 and (LH)-H-2 have been prepared. The ligands are synthesized by the condensation of 2-hydroxy-3-formylquinoline with salicyloylhydrazide and 2-hydrazinobenzothiazole in absolute ethanol. The prepared complexes were characterized by the analytical and spectral techniques. The stoichiometry of the complexes is found to be 1:1. The presence of coordinated and lattice water is confirmed by the TG and DTA studies. Subsequently all the prepared complexes were screened for antimicrobial activity against bacteria and fungi. The Cu(II) complexes have been found to be more active than the ligand. In addition the DNA binding/cleaving capacity of the compounds was analyzed by absorption spectroscopy, viscosity measurement, thermal denaturation, and gel electrophoresis methods.

  DOI：

  10.1007/s00044-010-9330-5

文献信息

• Crystal structures, DNA-binding and cytotoxic activities studies of Cu(II) complexes with 2-oxo-quinoline-3-carbaldehyde Schiff-bases
  作者：Zeng-Chen Liu、Bao-Dui Wang、Bo Li、Qin Wang、Zheng-Yin Yang、Tian-Rong Li、Yong Li

  DOI：10.1016/j.ejmech.2010.08.060

  日期：2010.11

  Three novel 2-oxo-quinoline-3-carbaldehyde Schiff-bases and their Cu(II) complexes were synthesized. The molecular structures of Cu(II) complexes were determined by X-ray crystal diffraction. The DNA-binding modes of the complexes were also investigated by UV vis absorption spectrum, fluorescence spectrum, viscosity measurement and EB-DNA displacement experiment. The experimental evidences indicated that the ligands and Cu(II) complexes could interact with CT-DNA (calf-thymus DNA) through intercalation, respectively. Comparative cytotoxic activities of ligands and Cu(II) complexes were also determined by MTT [3-(4,5-dimethyl-2-thiazoyl)-2,5-diphenyl-2H-tetrazolium bromide] and SRB (sulforhodamine B) methods. The results showed that the three Cu(II) complexes exhibited more effective cytotoxic activity against HL60 cells and HeLa cells than corresponding ligands. Also, CuL3 showed higher cytotoxic activity than CuL1 and CuL2 (C) 2010 Elsevier Masson SAS. All rights reserved.