13207-66-4Relevant articles and documents
Four tetra-nuclear lanthanide complexes based on 8-hydroxyquinolin derivatives: magnetic refrigeration and single-molecule magnet behaviour
Fang, Ming,Shao, Li-Jun,Shi, Tian-Xing,Chen, Ying-Ying,Yu, Hong,Li, Peng-Fei,Wang, Wen-Min,Zhao, Bin
, p. 11847 - 11853 (2018)
Four tetra-nuclear lanthanide complexes: {[Ln4(L)6(tmhd)4(μ3-OH)2]·mH2O} (Ln = Gd (1, m = 0), Tb (2, m = 3), Dy (3, m = 0), Ho (4, m = 0); L = 5-((pyridin-4-ylmethylene)amino)quinolin-8-ol, tmhd = 2,2,6,6-tetramethylheptane-3,5-dione) were fabricated and structurally characterized. Compounds 1-4 are isostructural and belong to the monoclinic system with space group P21/n. The cores of the complexes contain a tetranuclear arrangement of LnIII ions, which is bridged by the two pyramidal μ3-OH- ions, and the four LnIII ions are precisely coplanar. The magnetic study reveals that 1 exhibits cryogenic magnetic refrigeration property (-ΔSm = 20.85 J K-1 kg-1), whereas compound 3 exhibits slow relaxation of the magnetization.
The Synthesis of Quinoline-based Tin Complexes with Pendant Schiff Bases
Butler, Patrick W. V.,Ward, Jas S.
, p. 694 - 699 (2019)
Whilst pursuing the synthetic utility of quinoline-based tin complexes, Me2Sn(Quin-NO2)2 (1) and Ph2Sn(Quin-NO2)2 (2) (Quin-NO2 = 5-nitroquinolino-8-oate) were synthesized bearing coordinatively inert nitro groups. Conventional reduction methodologies successfully converted 1 to Me2Sn(Quin-NH2)2 (3) and 2 to Ph2Sn(Quin-NH2)2 (4) (Quin-NH2 = 5-aminoquinolino-8-oate). The synthetically useful amine groups proved difficult to exploit in the presence of the central tin atom, however, a complete Schiff base functionalized Sn complex of the dimethyltin pro-ligand Me2Sn(Quin-py)2 (6) was successfully synthesized from 5-[(pyridin-2-ylmethylene)amino]quinolin-8-ol (HQuin-py; 5) in good yield via an alternative strategy exploiting the oxophilic tendencies of tin. All species were fully characterized by NMR (including 119Sn NMR spectroscopy), HR-ESI MS and single-crystal X-ray diffraction, and preliminary studies of their supramolecular potential are also discussed.
Structures, magnetic refrigeration and single molecule-magnet behavior of five rhombus-shaped tetranuclear Ln(iii)-based clusters
Cui, Jian-Zhong,Fang, Ming,Gao, Hong-Ling,Huai, Lei,Jiang, Kai-Jun,Shen, Hai-Yun,Wang, Wen-Min,Wang, Xi-Wen
, p. 10266 - 10274 (2020)
A series of coplanar tetranuclear Ln(iii)-based clusters, namely [Ln4(acac)4(L)6(μ3-OH)2]·[solvent] (Ln = Eu (1), Gd (2), Tb (3), Dy (4) and Er (5)), have been synthesized by using an 8-hydroxyquinoline Schiff base ligand (HL = 5-(2-thenylidene)-8-hydroxylquinoline) and acetylacetone. Their structures and magnetic properties have been completely characterized. The structure determination shows that clusters 1-5 are isostructural with a rhombus-shaped Ln4 core. The magnetic studies reveal that the Gd4 cluster (2) displays cryogenic magnetocaloric effects with a maximum-ΔSm value of 22.09 J kg-1 K-1 at 2.5 K and ΔH = 7.0 T; while ac susceptibility measurements show that single molecule-magnet behavior is exhibited by the Dy4 cluster (4) with the anisotropic barrier (ΔE/kB) of 75.01 K. Interestingly, more than one maximal out-of-phase ac signals (χ′′) were observed in 4, suggesting the operation of multiple magnetic relaxation processes in 4. In addition, the solid state luminescence properties reveal that clusters 1, 3, and 4 display the characteristic lanthanum luminescence at room temperature. This journal is
Tetranuclear lanthanide complexes showing magnetic refrigeration and single molecule magnet behavior
Yu, Hong,Yang, Jia-Xing,Han, Ju-Qing,Li, Peng-Fei,Hou, Yin-Ling,Wang, Wen-Min,Fang, Ming
, p. 8067 - 8074 (2019/06/08)
Three tetranuclear lanthanide complexes: {[Ln4(L)6(pbd)4(μ3-OH)2]·2CH3CN} (Ln = Gd (1), Tb (2), Dy (3); HL = 5-(benzylideneamino)quinolin-8-ol, pbd = 1-phenylbutane-1,3-dione) were fabricated and structurally characterized. Compounds 1-3 are isostructural belonging to the triclinic system with space group P1. The core of the complexes contains a tetranuclear arrangement of LnIII ions which is held together by two pyramidal μ3-OH- ions and six μ2 phenol hydroxyl oxygen atoms derived from six L- ligands. Magnetic studies indicated that 1 exhibits cryogenic magnetic refrigeration properties (maximum -ΔSm = 21.41 J K-1 kg-1, ΔH = 7 T at 2.0 K), whereas compound 3 exhibits slow relaxation of the magnetization with an energy barrier (ΔE/kB) of 81.48 K and τ0 = 6.48 × 10-8 s.
G-quadruplex and duplex DNA binding studies of novel Ruthenium(II) complexes containing ascididemin ligands
Wumaier, Maierhaba,Shi, Jing-Jing,Yao, Tian-Ming,Hu, Xiao-Chun,Gao, Ru-Ru,Shi, Shuo
, (2019/04/17)
In this paper, three new Ruthenium(II) polypyridyl complexes containing ascididemin (ASC) as main ligand have been synthesized and characterized. Their interactions with different G-quadruplex (Htelo, c-myc and c-kit) (Htelo: human telomeric DNA, c-myc: cellular-myelocytomatosis viral oncogene, c-kit: oncogene c-kit promoter sequences) and duplex (ds26) DNA sequences were comparatively studied with the free ligand ASC by a series of spectroscopic techniques including UV–vis (ultraviolet-visible) spectroscopy, FID (fluorescent intercalator displacement) assay, and FRET (fluorescence resonance energy transfer) melting assay. Molecular docking studies were also performed to support the binding mode of the compounds with G-quadruplex DNA. Results indicated that [Ru(bpy)2ASC]·(PF6)2 (1), [Ru(phen)2ASC]·(PF6)2 (2), [Ru(tatp)2ASC]·(PF6)2 (3) (bpy = 2,2′?bipyridine, phen = 1,10?phenanthroline, tatp = 1,4,8,9?tetra?aza?triphenylene) and ASC can effectively bind G-quadruplex and duplex DNA and stabilization ability lies in the order 3 > 2 > 1 > ASC. Complex 3 was determined to be the most promising candidate for further in vitro studies and potential anticancer drug.
Study on Relationship Between Fluorescence Properties and Structure of Substituted 8-Hydroxyquinoline Zinc Complexes
Jianbo, He,Tingting, Zhou,Yongjing, Cao,Yuanyuan, Zhang,Weiqing, Yang,Menglin, Ma
, p. 1121 - 1126 (2018/08/17)
Organic light-emitting diodes (OLEDs) produced from 8-hydroxyquinoline metal complexes play a vital role in modern electroluminescent devices. In this manuscript, a series of 8-hydroxyquinoline derivatives were synthesized by different methods and their corresponding zinc metal complexes were prepared. The UV and fluorescence properties of the complexes were measured aiming to understand the effect of substituents at the quinoline ring on the fluorescence properties of the complexes. When the C-5 of 8-hydroxyquinoline was replaced by halogen group, the fluorescence emission wavelengths had been red-shifted, at the same time, blue-shifted of fluorescence emission wavelength was observed when the C-5 position of 8-hydroxyquinoline was substituted by electron-withdrawing group. When the C-4 position of 8-hydroxyquinolie was substituted by methyl or the C-5 position was substituted by sulfonic acid group, the corresponding zinc complexes had higher fluorescence intensity than 8-hydroxyquinolie zinc.
New Aryl Derivatives of Quinolinedione and Related Heterocyclic Compounds
Egu, Samuel Attah,Okoro, Uchechukwu Chris,Onoabedje, Efeturi Abraham
, p. 1572 - 1577 (2017/03/27)
The synthesis of new derivatives of 6,7-dibromoquinoline-5,8-dione and 6,7-dichloroquinoline-5,8-dione via palladium/Sphos-mediated Suzuki–Miyaura cross-coupling reaction is reported. The 6,7-dibromoquinoline-5,8-dione and 6,7-dichloroquinoline-5,8-dione intermediates were prepared in a three-step reaction from 8-hydroxyquinoline. The palladium-catalyzed reactions of 6,7-dibromoquinoline-5,8-dione and 6,7-dichloroquinoline-5,8-dione with a variety of aryl boronic acids provide coupled compounds in high yields. The arylation of 6,7-dibromoquinoline-5,8-dione and 6,7-dichloroquinoline-5,8-dione with 4-bromophenyl boronic acid supplied 6,6′-(1,4-phenylene)bis(7-bromoquinoline-5,8-dione) and (4-(6-(4-(6-chloro-5,8-dihydroquinolin-7-yl)phenyl)-5,8-dihydroquinolin-7-yl)phenyl)boronic acid respectively, in addition to the expected coupled compounds in moderate yields. Also, Pd(0)/PPh3 allowed the 7-chloro-6-(4-nitrophenyl)quinoline-5,8-dione and 7-chloro-6-phenylquinoline-5,8-dione to be synthesized via Heck reaction. The yields of the synthesized target molecules depend largely on the reaction conditions and the type of ligands employed. Structural assignments of the synthesized compounds were established by spectra and analytical data.
Synthesis of N-aryl and N-heteroaryl hydroxylamines via partial reduction of nitroarenes with soluble nanoparticle catalysts
Tyler, Jefferson H.,Nazari, S. Hadi,Patterson, Robert H.,Udumula, Venkatareddy,Smith, Stacey J.,Michaelis, David J.
supporting information, p. 82 - 86 (2016/12/23)
Polystyrene-supported ruthenium nanoparticles enable the selective hydrazine-mediated reduction of nitroarenes to hydroxylamine products in high yield and selectivity. Key to obtaining the hydroxylamine product in good yield was the use of organic solvents capable of solubilizing the polystyrene-supported nanoparticle catalyst. N-aryl and N-heteroaryl hydroxylamines are generated under exceptionally mild conditions and in the presence of a various easily reduced functional groups.
Design, synthesis and biological evaluation of ezrin inhibitors targeting metastatic osteosarcoma
Paige, Mikell,Kosturko, George,Bulut, Güllay,Miessau, Matthew,Rahim, Said,Toretsky, Jeffrey A.,Brown, Milton L.,üren, Aykut
, p. 478 - 487 (2014/01/17)
Respiratory failure due to pulmonary metastasis is the major cause of death for patients with osteosarcoma. However, the molecular basis for metastasis of osteosarcoma is poorly understood. Recently, ezrin, a member of the ERM family of proteins, has been associated with osteosarcoma metastasis to the lungs. The small molecule NSC 668394 was identified to bind to ezrin, inhibit in vitro and in vivo cell migration, invasion, and metastatic colony survival. Reported herein are the design and synthesis of analogues of NSC 668394, and subsequent functional ezrin inhibition studies. The binding affinity was characterized by surface plasmon resonance technique. Cell migration and invasion activity was determined by electrical cell impedance methodology. Optimization of a series of heterocyclic-dione analogues led to the discovery of compounds 21k and 21m as potential novel antimetastatic agents.
Synthesis, characterization, screening and docking analysis of 4-anilinoquinazoline derivatives as tyrosine kinase inhibitors
Lue, Shuang,Zheng, Wei,Ji, Liyun,Luo, Qun,Hao, Xiang,Li, Xianchan,Wang, Fuyi
, p. 84 - 94 (2013/04/23)
We report here the design and synthesis of a series of 4-anilinoquinazoline derivatives, of which 7 compounds were crystallographically characterized, as epidermal growth factor receptor (EGFR) inhibitors by modifications on the aniline ring or at the 6-alkoxy site of the 6,7-dimethoxy-4-anilinoquinazoline pharmacophore. The relative inhibition efficiency on EGFR of all as-prepared compounds were measured and ordered, and the IC50 values of nine highly active compounds were determined by ELISA. Docking studies indicated that all 4-anilinoquinazoline derivatives could be inserted into the ATP-binding pocket of the EGFR via indirect docking, and that the modifications at the 3′-position of the anilino group and 6-alkoxy site of the quinazoline ring have little interference with the formation of the two essential H-bonds between the N3 of the quinazoline ring and Thr766 through a water molecule, and the N1 of the quinazoline ring and N-H of Met769. The displacing of the phenyl at 4-position with pyridinyl dramatically reduces the activity of the quinazoline pharmacophore, the resulting derivative (10) being the least active compound. The docking results also showed that the formation of new H-bonds between the N-H of the ethylenediamine group linked to the 6-alkoxy site and Asp776/Cys773 in the binding pocket of EGFR makes compounds 19 (IC50 = 12.1 ± 1.6 nM) and 20 (IC50 = 13.6 ± 0.8 nM) the most potent EGFR inhibitors in this class and worthy of further modification to obtain more potent anticancer compounds.
