27037-61-2

Usage

InChI:InChI=1/C12H11NO2/c1-8-6-7-10-4-3-5-11(12(10)13-8)15-9(2)14/h3-7H,1-2H3

Upstream product

• 826-81-3 2-methyl-8-quinolinol 
• 108-24-7 acetic anhydride 

Downstream Products

• 14510-06-6 2-formyl oxine 

Relevant academic research and scientific papers

Antifungal styryloquinolines as candida albicans efflux pump inhibitors: Styryloquinolines are ABC transporter inhibitors

Styrylquinolines are heterocyclic compounds that are known for their antifungal and antimicrobial activity. Metal complexation through hydroxyl groups has been claimed to be a plausible mechanism of action for these types of compounds. A series of novel structures with protected hydroxyl groups have been designed and synthesized to verify the literature data. Their antifungal activity against wild-type Candida albicans strain and mutants with silenced efflux pumps activity has been determined. Combinations with fluconazole revealed synergistic interactions that were dependent on the substitution pattern. These results open a new route for designing active antifungal agents on a styrylquinoline scaffold.

A new 2-((Z)-thiosemicarbazidomethyl)-quinolin-8-YL acetate ligand and its Cu(II) complex: Syntheses, structures, and characterizations

A new ligand, 2-((Z)-thiosemicarbazidomethyl)-quinolin-8-yl acetate (C 13H12 N4O2S) (L) and its Cu(II) coordination complex, [Cu(L1)] [HL1 = (Z)-1-((8-hyd- roxyquinolin-2-yl)methylene)thiosemicarbazide], have been synthesized, and characterized by IR, elemental analysis, 1H NMR, MS, and X-ray single-crystal diffraction. L shows a stable three-dimensional supramolecular structure through hydrogen bonds and - stacking interactions. [Cu(L 1)] shows a three-dimensional network structure formed only by hydrogen bonds. In addition, the fluorescence spectra of L were measured. Copyright

Synthesis, structure, and luminescent properties of 2-[2-(9-Anthryl)vinyl] quinolines

Previously unknown 2-[2-(9-anthryl)vinyl]quinolin-8-ol and 2-[2-(9-anthryl)vinyl]-8-methoxyquinoline were synthesized by condensation of 8-hydroxy(methoxy)-2-methylquinoline with 9-anthraldehyde in acetic anhydride, as well as by the Wittig reaction. The product structure was determined on the basis of their 1H NMR, IR, UV, and mass spectra and quantum-chemical calculations. 2-[2-(9-Anthryl)vinyl]-8-methoxyquinoline showed luminescence with a quantum yield f of 0.25, which was considerably higher than that of its 8-hydroxy analog (f = 0.067). Pleiades Publishing, Ltd., 2012.

Octadentate oxine-armed bispidine ligand for radiopharmaceutical chemistry

In this study, we present the synthesis and characterization of the octadentate bispidine ligand, H2bispox2 and its complexes with medicinally useful radiometal nuclides (111In3+ and 177Lu3+), including their X-ray diffraction single crystal structures with the stable isotopes. 111InCl3 radiolabels the ligand quantitatively at ambient conditions ([L] = 10?5 M, room temperature, pH 7 and 15 min) and the in vitro human serum stability assays demonstrated high stability of the [111In(bispox2)]+ complex over 5 days. Moreover, the β? emitter 177Lu radiolabels the ligand at 37 °C in 30 min (pH 8). These initial investigations reveal the potential of the octadentate bispidine ligand H2bispox2 as a useful chelator for 111In and 177Lu-based radiopharmaceuticals.

Di(8-hydroxyquinoline) derivatives for supramolecular chemistry: Syntheses and solid state superstructures

The synthesis of the di(8-hydroxyquinoline) derivatives 8-14 is described. Hereby, spacers of different length and nature (alkyl or amide) are introduced. The geometric features of the compounds are changed by connection of the bridging groups to different positions of the 8- hydroxyquinoline moiety. The derivatives thus obtained possess a high potential as ligands for metallo-supramolecular chemistry. In the solid state the alkyl-bridged compounds adopt a polymeric structure by formation of hydrogenbridges between self-complementary hydroxyquinoline units. The overall structure of the polymer is controlled by the spacer. Introduction of an amide group in 7-position of the quinoline leads to intramolecular hydrogen bonds and suppresses the formation of 'dimeric' di(8- hydroxyquinoline) units.

Synthesis and luminescence properties of novel 8-hydroxyquinoline derivatives and their Eu(III) complexes

Six novel 8-hydroxyquinoline derivatives were synthesized using 2-methyl-8-hydroxyquinoline and para-substituted phenol as the main starting materials, and were characterized by 1H nuclear magnetic resonance (NMR), mass spectrometry (MS), ultraviolet (UV) light analysis and infra-red (IR) light analysis. Their complexes with Eu(III) were also prepared and characterized by elemental analysis, molar conductivity, UV light analysis, IR light analysis, and thermogravimetric–differential thermal analysis (TG–DTA). The results showed that the ligand coordinated well with Eu(III) ions and had excellent thermal stability. The structure of the target complex was EuY1–6(NO3)3.2H2O. The luminescence properties of the target complexes were investigated, the results indicated that all target complexes had favorable luminescence properties and that the introduction of an electron-donating group could enhance the luminescence intensity of the corresponding complexes, but the addition of an electron-withdrawing group had the opposite effect. Among all the target complexes, the methoxy-substituted complex (–OCH3) had the highest fluorescence intensity and the nitro-substituted complex (–NO2) had the weakest fluorescence intensity. The results showed that 8-hydroxyquinoline derivatives had good energy transfer efficiency for the Eu(III) ion. All the target complexes had a relatively high fluorescence quantum yield. The fluorescence quantum yield of the complex EuY3(NO3)3.2H2O was highest among all target complexes and was up to 0.628. Because of excellent luminescence properties and thermal stabilities of the Eu(III) complexes, they could be used as promising candidate luminescent materials.

Oxine based unsymmetrical (O?, N, S/Se) pincer ligands and their palladium(ii) complexes: synthesis, structural aspects and applications as a catalyst in amine and copper-free Sonogashira coupling

Unsymmetrical pincer ligands having an 8-hydroxyquinoline (oxine) core viz. 2-(phenylthio/selenomethyl) quinolin-8-ol (L1/L2), 2-(N,N-dimethylthiocarbamoyl) quinolin-8-ol (L3) and 2-(pyrrolidin-1-ylthiocarbamoyl) quinolin-8-ol (L4) were synthesized. 2-Met