[Cu(lawsone)₂(H₂O)₂] | 259249-66-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [Cu(lawsone)₂(H₂O)₂]
• 英文别名: [Cu(Lw)₂(H₂O)₂]
• CAS: 259249-66-6；808162-14-3
• 化学式: C₂₀H₁₄CuO₈
• 分子量: 445.872
• InChiKey: FLPJOEPMVRBPCR-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  [Cu(lawsone)₂(H₂O)₂] 以 neat (no solvent) 为溶剂， 生成 copper(II) oxide
  参考文献：
  名称：

  摘要：

  Copper(II) complexes of lawsone (2-hydroxy-1,4-naphthaquinone, Lw) with variety of aqua ligation viz. Cu-1, [Cu(Lw)(2)(H2O)](2); Cu-2, [Cu(Lw)(2)(H2O)(2)] and Cu-3, [Cu(Lw)(2)(H2O)(2)](2) have been synthesized. The role of water as counter ligand on coordination propensity of redox active lawsone in naphthoquinone/naphthosemiquinone (NQ/NSQ) forms is quantified by studies of pyrolytic reactions, using non-isothermal TG and DTA techniques, coupled with IR studies. Mixed (NQ) (NSQ) ligation in Cu-1 and Cu-3 required energy of activation, E-a similar to 67 kJ mol(-1) of (NQ) and similar to 41 kJ mol(-1) of (NSQ). Comparable energies of aqua ligand (similar to 43 kJ mol(-1)) with NSQ ligand in Cu-1 and Cu-3, dictate charge distributions in lawsone coordinations. A large difference between E-a of aqua and p-NQ ligand indicates coordination of lawsone in its fully oxidised quinone form in Cu-2. From thermoanalytical studies schematic oxidative decomposition mechanisms are proposed for Cu-1 and Cu-3. From pyrolytic reactions enthalpies are estimated by DTA technique.

  DOI：

  10.1023/a:1010121214059
• 作为产物：
  描述：

  copper(II) choride dihydrate 、 2-羟基-1,4-萘醌 在 sodium 作用下， 以 甲醇 为溶剂， 生成 [Cu(lawsone)₂(H₂O)₂]
  参考文献：
  名称：

  'Heena' (2-hydroxy-1,4-naphthoquinone) 的金属配合物：合成、表征和抗癌活性

  摘要：

  Henna 的 Mn(II)、Co(II)、Ni(II)、Cu(II) 和 Zn(II) 络合物；2-羟基-1,4-萘醌 ( Lw ) 在 0 °C 下合成（Mn 2+ ; 1 , Co 2+ ; 2 , Ni 2+ ; 3 , Cu 2+ ; 4和 Zn 2+ ; 5）， 26 °C (Mn 2+ ; 1A , Co 2+ ; 2A , Ni 2+ ; 3A , Cu 2+ ; 4A和 Zn 2+ ; 5A) 和特征。所有配合物的组成都是[M(Lw) 2 (H 2 O) 2 ]类型。在 26 °C 下合成的复合物的几何结构为反式，而在 0 °C 下复合物4为顺式。铜配合物4A的吡啶加合物 ( 4Apy ) 和配合物4的甲醇 ( 4MeOH ) 加合物通过单晶 X 射线衍射研究表征。从2A、5A、4Apy和4MeOH的 X 射线结构揭示了分子相互作用. 针对两种癌细胞系 MCF-7（乳腺癌细胞系）和

  DOI：

  10.1016/j.ica.2022.121290

文献信息

• Synthesis and cytotoxic activity of metallic complexes of lawsone
  作者：Sandra Oramas-Royo、Concepción Torrejón、Irene Cuadrado、Rita Hernández-Molina、Sonsoles Hortelano、Ana Estévez-Braun、Beatriz de las Heras

  DOI：10.1016/j.bmc.2013.03.002

  日期：2013.5

  In the present study, a series of metallic complexes of the 1,4-naphthoquinone lawsone (2-6) were synthesized and evaluated for potential cytotoxicity in a mouse leukemic macrophagic RAW 264.7 cell line. Cell viability was determined by the MTT assay. Significant growth inhibition was observed for the copper complex (4) with an IC50 value of 2.5 mu M. This compound was selected for further evaluation of cytotoxic activity on several human cancer cells including HT-29 (human colorectal adenocarcinoma), HepG2 (human hepatocellular carcinoma) and HeLa, (human cervical adenocarcinoma cells). Significant cell viability decrease was also observed in HepG2 cells. The apoptotic potential of this complex was evaluated in these cells. Compound 4 induced apoptosis by a mechanism that involves the activation of caspases 3, 8 and 9 and modulation of apoptotic-related proteins such as Bax, Bad, and p53. These results indicate that metal complexes of lawsone derivatives, in particular compound 4, might be used for the design of new antitumoral agents. (C) 2013 Elsevier Ltd. All rights reserved.
• Three dimensional hydrogen-bonding network in a copper complex of 2-hydroxy-1,4-naphthoquinone: structural, spectroscopic and magnetic properties
  作者：S. Salunke-Gawali、S.Y. Rane、V.G. Puranik、C. Guyard-Duhayon、F. Varret

  DOI：10.1016/j.poly.2004.08.022

  日期：2004.10

  Supramolecular [Cu(II)(ONQ)(2)(H2O)(2)](n) (1) a complex of the 2-hydroxy-1,4-naphthoquinone ligand (2HNQ), has been synthesized using CuCl2 . 2H(2)O. ONQ is the deprotonated oxidized form of the ligand (viz. 2-oxido-1,4-naphthoquinone). The complex has been characterised by X-ray crystallography, variable temperature magnetic susceptibility measurements (SQUID), EPR and CV studies. The crystal structure of 1 has been solved at 295 and 161 K. The cell volume decreases from 435.3(6) Angstrom(3) at 295 K to 427.9(6) Angstrom(3) at 161 K. The monomeric units of 1 are linked by three types of intermolecular hydrogen bondings through coordinated ONQ ligands and water molecules, which results in a supramolecular three dimensional hydrogen bonding network. The magnetic susceptibility data of I were best fitted with the Bonner Fisher equation with the coupling parameter J = -3.2 cm(-1), indicating a weak antiferromagnetic interaction along the chain. (C) 2004 Elsevier Ltd. All rights reserved.