27525-74-2Relevant articles and documents
Light-Stimulated Generation of Free Radicals by Quinones-Chelators
Markova, Irina D.,Polyakov, Nikolay E.,Selyutina, Olga Yu.,Fedenok, Lidia G.,Fedotov, Kirill Yu.,Slepneva, Irina A.,Leshina, Tatyana V.,Pokrovsky, Andrey G.,Vasilieva, Nadezhda V.,Weiner, Lev M.
, p. 369 - 389 (2017)
The role of metal ions in the mechanism of light-stimulated redox activity of potential anticancer agent 2-phenyl-4-(butylamino)naphtha[2,3-h]quinoline-7,12-dione (Qc) has been studied by CIDNP (chemically induced dynamic nuclear polarization) and EPR methods. The photo-induced oxidation of NADH and its synthetic analog-substituted dihydropyridine (DHP)-by quinone Qc was used as a model. The Qc capability of producing chelating complexes with divalent metal ions of Fe, Zn and Ca was studied quantitatively by optical absorption spectroscopy. A significant decrease of electrochemical reduction potential of Qc (ΔE=0.4-0.6 eV for ACN and ACN/PBS solutions) in chelating complexes and in protonated form of Qc was observed. A pronounced increase in efficiency of DHP oxidation in chelating complexes with Zn2+ and Ca2+ ions compared with free Qc was demonstrated. The yields of free radicals, including reactive oxygen species (ROS) and reaction products, were a few times higher than those in the absence of metal ions. Application of such chelating compounds to enhance ROS generation looks very promising for anti-cancer therapy, including the photodynamic therapy.
Direct and co-catalytic oxidative aromatization of 1,4-dihydropyridines and related substrates using gold nanoparticles supported on carbon nanotubes
Prakash, Praveen,Gravel, Edmond,Li, Haiyan,Miserque, Frédéric,Habert, Aurélie,Den Hertog, Martien,Ling, Wai Li,Namboothiri, Irishi N. N.,Doris, Eric
, p. 6476 - 6479 (2016)
A heterogeneous catalyst was assembled by stabilization of gold nanoparticles on carbon nanotubes. The resulting nanohybrid was used in the catalytic aerobic oxidation of 1,4-dihydropyridines. The system proved very efficient on the investigated substrates either directly or in the presence of a quinone co-catalyst.
Transition-Metal-Free Alkylation and Acylation of Benzoxazinones with 1,4-Dihydropyridines
Byun, Youjung,Moon, Junghyea,An, Won,Mishra, Neeraj Kumar,Kim, Hyung Sik,Ghosh, Prithwish,Kim, In Su
, p. 12247 - 12256 (2021/09/07)
The direct functionalization of N-heterocycles is a vital transformation for the development of pharmaceuticals, functional materials, and other chemical entities. Herein, the transition-metal-free alkylation and acylation of C(sp2)-H bonds in biologically relevant 2-benzoxazinones with 1,4-dihydropyridines as readily accessible radical surrogates is described. Excellent functional group compatibility and a broad substrate scope were attained. Gram-scale reaction and transformations of the synthesized adducts via Suzuki coupling with heteroaryl boronic acids demonstrated the synthetic potential of the developed protocol.
Method for synthesizing pyridine and derivatives thereof by catalyzing Hanss ester 1, 4-dihydropyridine compound through titanocene dichloride
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Paragraph 0013-0017; 0043-0047, (2021/07/28)
The invention discloses a method for synthesizing pyridine and derivatives thereof by catalyzing a Hass ester 1, 4-dihydropyridine compound through titanocene dichloride, the dihydropyridine structure of the Hass ester 1, 4-dihydropyridine compound has a certain aromatic ring driving force and is easily oxidized into a pyridine structure, and the the Hass ester 1, 4- dihydropyridine and the derivative thereof are subjected to oxidative conversion to generate the pyridine and the derivative thereof by taking titanocene dichloride as a catalyst, so that a simple way for preparing the pyridine and the derivative thereof is provided. The method is mild in reaction condition, simple to operate, short in reaction time, single in reaction product and high in atom economy, and only the product needs to be subjected to simple column chromatography separation after the reaction is finished. The Hanss ester 1, 4-dihydropyridine and the derivative thereof obtained by the invention have wide biological activity and medicinal value.