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 efficient synthesis of 4H-chromene, 4H-pyran, and oxepine derivatives via one-pot three-component tandem reactions
Kazemi, Bagher,Javanshir, Shahrzad,Maleki, Ali,Safari, Mostafa,Khavasi, Hamid Reza
, p. 6977 - 6981 (2012)
A new and efficient method has been developed for the synthesis of highly functionalized 2-amino-4H-pyran, 2-amino-4H-chromene, 2-amino-oxepine, and 2-hydroxy-oxepine derivatives through one-pot, three-component tandem reactions of structurally diverse 1,3-diketones, dialkyl acetylenedicarboxylates, and malononitrile or ethyl cyanoacetate in the presence of a catalytic amount of Na2CO3 in ethanol. This efficient technique has the advantages of giving products in good to high yields, in short reaction times, and with a simple isolation procedure.
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 and halocyclization of 3-cyano-4,6-dimethyl-2-pyridone allyl derivatives
Kim, Dmitry G.,Kalita, Elena V.,Sharutin, Vladimir V.,Ovchinnikova, Irina G.,Ezhikova, Marina А.,Kodess, Mikhail I.,Slepukhin, Pavel А.,Vasilenko, Anna V.
, p. 566 - 572 (2019)
[Figure not available: see fulltext.] The sequence of condensation, alkylation, and halocyclization reactions during the synthesis of the target 2,3-dihydro[1,3]oxazolo[3,2-a]-pyridinium salts was investigated. The effect of basic catalysis on the chemoselectivity of the reaction of malononitrile with acetylacetone has been revealed. In neutral media, the selectivity of the formation of 3-cyano-4,6-dimethyl-2-pyridone increases. The presence of Et3N, on the other hand, leads to the formation of side products. Allylation of 3-cyano-4,6-dimethyl-2-pyridone proceeds with the formation of regioisomeric 1-allyl-3-cyano-4,6-dimethyl-2-pyridone and 2-allyl-3-cyano-4,6-dimethyloxypyridine in a 3:1 ratio, while the high chemoselectivity of halocyclization of allyl derivatives with iodine or bromine results in practically quantitative yields of 2,3-dihydro[1,3]oxazolo[3,2-a]pyridinium salts.
Discovery of quinolone derivatives as antimycobacterial agents
Gao, Chao,Li, Xiao,Liu, Kun-Lin,Teng, Fei,Xiong, Lu,Yu, Luo-Ting
, p. 24095 - 24115 (2021/07/29)
Tuberculosis (TB), an infectious disease caused byMycobacterium tuberculosis(M. tuberculosis), is an important public health issue. Current first-line drugs administered to TB patients have been in use for over 40 years, whereas second-line drugs display strong side effects and poor compliance. Additionally, designing effective regimens to treat patients infected with multi- and extremely-drug-resistant (MDR and XDR) strains of TB is challenging. In this report, we screened our compound library and identified compound1with antituberculosis activity and a minimal inhibitory concentration (MIC) againstM. tuberculosisof 20 μg mL?1. Structure optimization and the structure-activity relationship of1as the lead compound enabled the design and synthesis of a series of quinolone derivatives,6a1-6a2,6b1-6b36,6c1,6d1-6d14,7a1-7a2,7b1-7b2,7c1,8a1-8a5,9a1-9a4and10a1-10a6. These compounds were evaluatedin vitrofor anti-tubercular activity against theM. tuberculosisH37Rv strain. Among them, compounds6b6,6b12and6b21exhibited MIC values in the range of 1.2-3 μg mL?1and showed excellent activity against the tested MDR-TB strain (MIC: 3, 2.9 and 0.9 μg mL?1, respectively). All three compounds were non-toxic toward A549 and Vero cells (>100 and >50 μg mL?1, respectively). In addition, an antibacterial spectrum test carried out using compound6b21showed that this compound specifically inhibitsM. tuberculosis. These can serve as a new starting point for the development of anti-TB agents with therapeutic potential.
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.
Chelating behavior of 3-amino-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine ligand towards some metal ions, spectral and thermal measurements as well as molecular modeling and biological studies
Masoud, Mamdouh S.,AbouEl-Enein, Saeyda A.,Ali, Alaa E.,Abd Elhamed, Eman H.
, (2019/10/28)
The 3-amino-4,6-dimethyl-1H-pyrazolo [3,4-b]pyridine ligand and its Mn(II), Pd(II), Fe(III), Cr(III), Ru(III), Hf(IV), Zr(IV) and UO2(II) metal complexes were synthesized and characterized by means of elemental analysis, spectral studies and thermal investigation. Also, the theoretical studies that done by Spartan ‘14 V1.1.4 software supported the experimental studies. The infrared data suggest that the ligand coordinates to the metal ions as a neutral monodentate moiety through nitrogen atom of amino group. The complexes are formed with 1:2 and 1:3 (M:L) molar ratios. All complexes possesses octahedral geometry except the Pd(II) complex that presents a square planar geometry. Thermal analyses (TGA and DTG) of ligand and its metal complexes are performed in order to identify the external solvents molecules and thermal stability ranges of the complexes. The X-ray diffraction studies suggest orthorhombic structure of P type lattice for Pd(II) complex and monoclinic structure of P type lattice for Cr(III) and Zr(IV). Theoretical calculations are performed to corroborate the experimental results. Some theoretical parameters are reported in order to compare the reactivity of the compounds. The cytotoxic activity of the ligand and its Pd(II) and Ru(III) complexes is evaluated against breast MCF-7 cell line. Pd(II) complex presents a higher activity. The synthesized ligand and its Pd(II), Cr(III) and Zr(IV) metal complexes also are screened for antibacterial activity. The ligand and its tested complexes has weak activity towards a Gram-positive bacteria and no activity towards Gram-negative bacteria except Pd(II) complex.
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.
5-Hydroxyindole-based EZH2 inhibitors assembled via TCCA-catalyzed condensation and Nenitzescu reactions
Chen, Guoliang,Du, Fangyu,Sun, Wenjiao,Wang, Lihui,Wu, Chunfu,Yang, Cheng,Zhou, Qifan
supporting information, (2020/05/16)
5-Hydroxyindole derivatives have various demonstrated biological activities. Herein, we used 5-hydroxyindole as a synthetic starting point for structural alterations in a combinatorial process to synthesize 22 different compounds with EZH2 inhibitor pharmacophores. A series of 5-hydroxyindole-derived compounds were screened inhibitory activities against K562 cells. According to molecular modeling and in vitro biological activity assays, the preliminary structure-activity relationship was summarized. Compound L–04 improved both the H3K27Me3 reduction and antiproliferation parameters (IC50 = 52.6 μM). These findings revealed that compound L–04 is worthy of consideration as a lead compound to design more potent EZH2 inhibitors. During the preparation of compounds, we discovered that trichloroisocyanuric acid (TCCA) is a novel catalyst which demonstrates condensation-promoting effects. To gain insight into the reaction, in situ React IR technology was used to confirm the reactivity. Different amines were condensed in high yields with β-diketones or β-ketoesters in the presence of TCCA to afford the corresponding products in a short time (10~20 min), which displayed some advantages and provided an alternative condensation strategy.
