15599-52-7Relevant articles and documents
New aryloxy-quinone derivatives as potential anti-Chagasic agents: synthesis, trypanosomicidal activity, electrochemical properties, pharmacophore elucidation and 3D-QSAR analysis
Vzquez, Karina,Espinosa-Bustos, Christian,Soto-Delgado, Jorge,Tapia, Ricardo A.,Varela, Javier,Birriel, Estefana,Segura, Rodrigo,Pizarro, Jaime,Cerecetto, Hugo,Gonzlez, Mercedes,Paulino, Margot,Salas, Cristian O.
, p. 65153 - 65166 (2015)
A set of new aryloxy-quinones were synthesized and evaluated in vitro against the epimastigote form of Trypanosoma cruzi and their unspecific cytotoxicity was tested on murine macrophages J-774 cells. Most of these novel compounds were found to be much more potent and selective than the standard drug nifurtimox. Interestingly, 2-phenoxy-naphthoquinone 3b displayed a remarkable nanomolar inhibitory activity, IC50 = 20 nM, and a high selectivity index, SI = 625. The Epc1 was determined for the most interesting compounds and no correlation with the trypanosomicidal effect was found. Therefore, an in silico study was carried out to obtain a pharmacophoric model and quantitative structure-trypanosomicidal activity relationship. The designed pharmacophore recognized the more potent and selective molecules, exhibiting five pharmacophoric features. A correlation coefficient R2 of 0.99 of pIC50 plotted against the predicted values indicated that the 3D-QSAR equation could be applied to further predictions of newly designed trypanosomicidal compounds.
Three Mn(ii) coordination polymers with a bispyridyl-based quinolinate ligand: The anion-controlled tunable structural and magnetic properties
Yuan, Guozan,Shan, Weilong,Liu, Bin,Rong, Lulu,Zhang, Liyan,Zhang, Hui,Wei, Xianwen
, p. 9777 - 9785 (2014)
Three new Mn(ii) coordination polymers, namely [Mn3L 6·2H2O] (1), [MnL2] (2), and [MnL 2·2H2O] (3), were prepared by solvothermal reactions of Mn(ii) salts with a bispyridyl-based quinolinate ligand. All complexes were characterized by elemental analysis, IR spectra, powder and single-crystal X-ray crystallography. Single crystal X-ray studies show that these coordination polymers exhibit a structural diversification due to the different counteranions (OAc-, Cl-, and NO 3-). Complex 1 has a 2D supramolecular structure with a cyclic tetramer Mn3L6 secondary building unit. Complex 2 possesses a rhombohedral grid network containing a type of meso-helical chain (P + M) constructed via the metal-ligand coordination interaction. Complex 3 features a 3D non-porous structure based on the arrangement of 2D grids. Magnetic susceptibility measurements indicate that the three Mn(ii) polymers 1-3 show disparate magnetic properties due to their different supramolecular structures.
Discovery of quinoline small molecules with potent dispersal activity against methicillin-resistant Staphylococcus aureus and Staphylococcus epidermidis biofilms using a scaffold hopping strategy
Abouelhassan, Yasmeen,Garrison, Aaron T.,Burch, Gena M.,Wong, Wilson,Norwood, Verrill M.,Huigens, Robert W.
, p. 5076 - 5080 (2014)
Staphylococcus aureus and Staphylococcus epidermidis are recognized as the most frequent cause of biofilm-associated nosocomial and indwelling medical device infections. Biofilm-associated infections are known to be highly resistant to our current arsenal of clinically used antibiotics and antibacterial agents. To exacerbate this problem, no therapeutic option exists that targets biofilm-dependent machinery critical to Staphylococcal biofilm formation and maintenance. Here, we describe the discovery of a series of quinoline small molecules that demonstrate potent biofilm dispersal activity against methicillin-resistant S. aureus and S. epidermidis using a scaffold hopping strategy. This interesting class of quinolines also has select synthetic analogues that demonstrate potent antibacterial activity and biofilm inhibition against S. aureus and S. epidermidis.
Three rare earth coordination compounds with selective inhibition effect on human ovarian cancer cells, preparation method and applications thereof
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Paragraph 0031-0033, (2020/04/02)
The invention discloses three rare earth coordination compounds with selective inhibition effect on human ovarian cancer cells, a preparation method and applications thereof, wherein the molecular formula of the rare earth coordination compound is (Et3NH)[Ln(C10H6NOBr2)4].H2O.DMF, and Ln represents Tb(III), Ho(III) or Er(III). The preparation method comprises the following steps: putting 2-methyl-5,7-dibromo-8-hydroxyquinoline and nitrate of a rare earth metal into a mixed solvent, dissolving, regulating the pH value of the system to 7.5-8.3 by using triethylamine, reacting under a heating condition, standing the reactant, separating out crystals, and collecting the crystals to obtain the corresponding target coordination compound. According to the invention, the test results show that thethree rare earth coordination compounds can selectively inhibit human ovarian cancer cells, are remarkable in activity and are expected to be developed into antitumor drugs.
Low-toxicity rare earth coordination compounds, preparation method and applications thereof
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Paragraph 0023-0025, (2020/05/01)
The invention discloses two low-toxicity rare earth coordination compounds, a preparation method and applications thereof, wherein the two coordination compounds are respectively a coordination compound 1 or a coordination compound 2, the molecular formula of the coordination compound 1 is [Eu(C10H6NOBr2)3(H2O)], and the molecular formula of the coordination compound 2 is [Gd(C10H6NOBr2)3(H2O)]. The preparation method comprises the following steps: taking 2-methyl-5,7-dibromo-8-hydroxyquinoline and europium nitrate hexahydrate or gadolinium nitrate hexahydrate, dissolving with a mixed solvent,adjusting the pH value of the obtained solution to 6.5-8.1, and reacting the obtained mixed solution under a heating condition to obtain a corresponding target product. The test results show that thetwo rare earth coordination compounds have significant inhibitory activity (the inhibitory activity is significantly higher than the inhibitory activity of cis-platinum) on tumor cell strains, have low toxicity on normal hepatocytes, and are expected to be developed into antitumor drugs.
Two rare earth coordination compounds constructed on the basis of 2-methyl-5,7-dibromo-8-hydroxyquinoline, preparation method and applications thereof,
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Paragraph 0027-0029, (2020/04/17)
The invention discloses two rare earth coordination compounds constructed on the basis of 2-methyl-5,7-dibromo-8-hydroxyquinoline, a preparation method and applications thereof, wherein the two coordination compounds are respectively a coordination compound 1 or a coordination compound 2, the molecular formula of the coordination compound 1 is [Sm(C10H6NOBr2)3(H2O)], and the molecular formula of the coordination compound 2 is [Tm(C10H6NOBr2)3(H2O)]. The preparation method of the rare earth coordination compound comprises the following steps: taking 2-methyl-5,7-dibromo-8-hydroxyquinoline and asamarium nitrate hexahydrate or thulium nitrate hexahydrate, dissolving with a mixed solvent, adjusting the pH value of the obtained solution to 6.5-8.1, and reacting the obtained mixed solution under a heating condition to obtain a corresponding target product. Test results show that the two rare earth coordination compounds have remarkable anti-proliferation effect on SK-OV-3 cell strains, havesignificantly high inhibition activity compared with cis-platinum, and are expected to be developed into anti-tumor drugs.
To 2 - methyl - 5, 7 - dibromo -8 - hydroxy quinoline as ligands of the single nucleus arrowhead complex and its preparation method and application
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Paragraph 0029; 0030, (2019/02/19)
The invention discloses a mononuclear dysprosium complex using 2-methyl-5,7-dibromo-8-hydroxyquinoline as a ligand and a preparation method and application thereof. A chemical formula of the complex is: [Dy(L)3(HL)], wherein L represents a product obtained after hydrogen atom of hydroxyl is removed from 2-methyl-5,7-dibromo-8-hydroxyquinoline, and has one unit of negative charges; HL represents 2-methyl-5,7-dibromo-8-hydroxyquinoline; the complex belongs to a triclinic system and a P-1 space group. The preparation method of the complex, which is disclosed by the invention, comprises: taking Dy(NO3)3.6H2O and 2-methyl-5,7-dibromo-8-hydroxyquinoline; dissolving Dy(NO3)3.6H2O and 2-methyl-5,7-dibromo-8-hydroxyquinoline with methanol; regulating pH of the obtained solution into a range of 6.0 to 7.5; performing a reaction on the obtained mixed solution under the heating condition to obtain the mononuclear dysprosium complex. The complex provided by the invention is simple in preparation method, low in cost and good in repeatability, shows a field-induced slow relaxation magnetic behavior at a low temperature, and can be used for preparing a magnetic material.
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.
Application of 5,7-dibromo-8-(methoxymethoxyl)-2-methylquinoline or pharmaceutical salt thereof to treatment on breast cancer
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Paragraph 0032; 0033, (2019/02/25)
The invention discloses application of 5,7-dibromo-8-(methoxymethoxyl)-2-methylquinoline or pharmaceutical salt thereof to treatment on breast cancer, and belongs to the technical field of biologicalmedicine. The 5,7-dibromo-8-(methoxymethoxyl)-2-methylquinoline is a quinoline derivative, which is called DBMMQ for short; the pharmaceutical salt is pharmaceutically acceptable salt, comprises saltformed by the 5,7-dibromo-8-(methoxymethoxyl)-2-methylquinoline and inorganic acid such as phosphoric acid, hydrochloric acid and sulfuric acid, and also comprises salt formed by the 5,7-dibromo-8-(methoxymethoxyl)-2-methylquinoline and organic acid such as citric acid and tartaric acid. The experiment indicates that the compound DBMMQ can not only obviously inhibit proliferation of various humanbreast cancer cells and induce apoptosis, but also has ability of inhibiting migration and invasion of the human breast cancer cells, and embodies high potential of resisting breast cancer; furthermore, the compound is easy to prepare and is further developed to be expected to provide a new choice for clinical breast cancer treatment.
Microwave-enhanced Friedl?nder synthesis for the rapid assembly of halogenated quinolines with antibacterial and biofilm eradication activities against drug resistant and tolerant bacteria
Garrison, Aaron T.,Abouelhassan, Yasmeen,Yang, Hongfen,Yousaf, Hussain H.,Nguyen, Tho J.,Huigens, Robert W.III.
supporting information, p. 720 - 724 (2017/04/27)
Herein, we disclose the development of a catalyst- and protecting-group-free microwave-enhanced Friedl?nder synthesis which permits the single-step, convergent assembly of diverse 8-hydroxyquinolines with greatly improved reaction yields over traditional oil bath heating (increased from 34% to 72%). This rapid synthesis permitted the discovery of novel biofilm-eradicating halogenated quinolines (MBECs = 1.0-23.5 μM) active against MRSA, MRSE, and VRE. These small molecules exhibit activity through mechanisms independent of membrane lysis, further demonstrating their potential as a clinically useful treatment option against persistent biofilm-associated infections.
