769-28-8Relevant articles and documents
Kinetics and Mechanism of the Condensation Reaction of Symmetrical and Unsymmetrical 1,3-Diketones with Cyanoacetamide in the Synthesis of 4,6-Disubstituted-3-cyano-2-pyridones
Misic-Vukovic, Milica,Radojkovic-Velickovic, Mirjana
, p. 1965 - 1970 (1992)
The rate constants for the condensation of cyanoacetamide with pentane-2,4-dione, 5-methylhexane-2,4-dione and 5,5-dimethylhexane-2,4-dione catalysed by piperidine were determined under a variety of experimental conditions.A UV spectrophotometric method for rate measurements was developed and the structures of the products were elucidated by means of a spectroscopic study.On the basis of the obtained rate constants, activation parameters and the evidence on the structure of synthesized unsymmetrical 4,6-disubstituted-3-cyano-2-pyridones a possible reaction scheme was suggested.It was thus possible to explain the selectivity of the reaction and the position of substituents in the pyridones obtained.
An Unusual Photodimerisation of a Pyrone Analogue; X-Ray Crystal Structure of the Principal Product
Alcock, Nathaniel W.,Samuel, Christopher J.
, p. 603 - 604 (1982)
Irradiation of 4-dicyanomethylene-2,6-dimethyl-4H-pyran (1) in methanol leads to the dimers (2) and (3); the structure of (2) has been determined by X-ray crystallography.
Synthesis, physicochemical and vibrational spectral properties of 2–pyridone and 2–aminopyridine derivatives: An experimental and theoretical study
El–Tahawy, Mohsen M. T.,Garavelli, Marco,Keshk, Reda M.
, (2020/09/01)
A convenient and efficient one–pot three–component reaction of acetyl acetone, malononitrile and ammonium acetate was investigated for the synthesis of 3–cyano–4,6–dimethyl–2–pyridone (PI) and 2–amino–3–cyano–4,6–dimethylpyridine (PII). The products were achieved with high purity, high yields and short reaction time. The yields of the two products depend on the concentration of ammonium acetate, reaction time and the solvent used. The structures of the isolated products were confirmed by elemental analysis and spectral data, supported by quantum chemical (MP2) calculations, both in gas phase and solvents (water and ethanol), that were also employed to track the reaction mechanisms and model vibrational spectral properties for final characterization and interpretation of spectral data. A remarkable matching between theoretical predictions and experiments was attained both for the geometrical parameters, as compared to X-Ray data available in the literature, and for vibrational frequencies, leading to a correlation coefficient (R2) of 0.99. Molecular docking was further studied to predict the docking binding energy of the synthesized compounds with the target proteins.
Anibamine and Its Analogues: Potent Antiplasmodial Agents from Aniba citrifolia
Du, Yongle,Valenciano, Ana Lisa,Dai, Yumin,Zheng, Yi,Zhang, Feng,Zhang, Yan,Clement, Jason,Goetz, Michael,Kingston, David G. I.,Cassera, Maria B.
supporting information, p. 569 - 577 (2019/10/16)
In our continuing search for novel natural products with antiplasmodial activity, an extract of Aniba citrifolia was found to have good activity, with an IC50 value less than 1.25 μg/mL. After bioassay-directed fractionation, the known indolizinium alkaloid anibamine (1) and the new indolizinium alkaloid anibamine B (2) were isolated as the major bioactive constituents, with antiplasmodial IC50 values of 0.170 and 0.244 μM against the drug-resistant Dd2 strain of Plasmodium falciparum. The new coumarin anibomarin A (3), the new norneolignan anibignan A (5), and six known neolignans (7-12) were also obtained. The structures of all the isolated compounds were determined based on analyses of 1D and 2D NMR spectroscopic and mass spectrometric data, and the absolute configuration of anibignan A (5) was assigned from its ECD spectrum. Evaluation of a library of 28 anibamine analogues (13-40) indicated that quaternary charged analogues had IC50 values as low as 58 nM, while uncharged analogues were inactive or significantly less active. Assessment of the potential effects of anibamine and its analogues on the intraerythrocytic stages and morphological development of P. falciparum revealed substantial activity against ring stages for compounds with two C-10 side chains, while those with only one C-10 side chain exhibited substantial activity against trophozoite stages, suggesting different mechanisms of action.
Synthesis and Photophysical Properties of 3-Amino-4-arylpyridin-2(1 H)-ones
Abramov, Anton A.,Chernenko, Sergey A.,Fisyuk, Alexander S.,Kostyuchenko, Anastasia S.,Shatsauskas, Anton L.
, p. 227 - 238 (2019/12/28)
A method has been developed for the preparation of oxazolo-[5,4- b ]pyridin-2(1 H)-ones based on the Hoffmann reaction of 2-oxo-1,2-dihydropyridine-3-carboxamides. Hydrolysis of oxazolo[5,4- b ]pyridin-2(1 H)-ones and the Hoffmann reaction of 2-oxo-1,2-dihydropyridine-3-carboxamides yielded 3-aminopyridin-2(1 H)-ones, including 4-aryl substituted derivatives in the series, for which effective phosphors with a quantum yield of up to 0.78 were detected. Photophysical properties of 3-aminopyridin-2(1 H)-ones were studied by UV and luminescence spectroscopy methods, and the relationship between their structure and photophysical properties was revealed.
