- An efficient green protocol for the preparation of acetoacetamides and application of the methodology to a one-pot synthesis of Biginelli dihydropyrimidines. Expansion of dihydropyrimidine topological chemical space
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The present study describes the preparation of N-aryl-(15) and N-alkyl-(17) acetoacetamides, in good to excellent yields, using both conventional and microwave heating, by reaction of amine derivatives (14 and 16) with 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD, 12) in aqueous medium. The acetoacetamides were used to prepare novel Biginelli dihydropyrimidine derivatives. The introduction of the amino acid derivatives potentially allows for the exploration of new structural complexity and topologically diversifies the chemical space occupied by this versatile chemical scaffold.
- Gama, Fernando H. S.,De Souza, Rodrigo O. M. A.,Garden, Simon J.
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p. 70915 - 70928
(2015/09/08)
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- Vinyl polymerizations of norbornene catalyzed by nickel complexes with acetoacetamide ligands
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On the basis of a remote effect, a series of acetoacetamide ligands and corresponding nickel complexes N-(R-phenyl) acetoacetamide Ni(CH2Ph) (PMe3) (R = H, 1; R = 2-methyl, 2; R = 2,6-dimethyl, 3; R = 2,6-diisopropyl, 4; R = 4-NO2, 5) were synthesized and characterized. The solid structure of complex 3 was confirmed by X-ray single-crystal analysis to be of cis form. 1H and 31P NMR spectroscopy confirmed that cis and trans isomers of nickel complexes were present in solution. Norbornene polymerizations with acetoacetamide nickel complexes activated with modified methylaluminoxane (MMAO) were investigated in detail. Remote steric and electronic effects of acetoacetamide ligand on catalytic activity and molecular weight of polynorbornenes (PNBs) were observed. Characterizations of the obtained PNBs show that the obtained polymer products are non-crystalline vinylic-addition polynorbornenes. Copyright
- Feng, Qian,Chen, Dajun,Feng, Danyang,Jiao, Libin,Peng, Zhigang,Pei, Lixia
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- Inhibitors of tick-borne flavivirus reproduction from structure-based virtual screening
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Flaviviruses form a large family of enveloped viruses affecting millions of people over the world. To date, no specific therapy was suggested for the infected people, making the treatment exclusively symptomatic. Several attempts were performed earlier for the design of fusion inhibitors for mosquito-borne flaviviruses, whereas for the tick-borne flaviviruses such design had not been performed. We have constructed homology models of envelope glycoproteins of tick-transmitted flaviviruses with the detergent binding pocket in the open state. Molecular docking of substituted 1,4-dihydropyridines and pyrido[2,1-b][1,3,5]thiadiazines was made against these models, and 89 hits were selected for the in vitro experimental evaluation. Seventeen compounds showed significant inhibition against tick-borne encephalitis virus, Powassan virus, or Omsk hemorrhagic fever virus in the 50% plaque reduction test in PEK cells. These compounds identified through rational design are the first ones possessing reproduction inhibition activity against tick-borne flaviviruses.
- Osolodkin, Dmitry I.,Kozlovskaya, Liubov I.,Dueva, Evgenia V.,Dotsenko, Victor V.,Rogova, Yulia V.,Frolov, Konstantin A.,Krivokolysko, Sergey G.,Romanova, Ekaterina G.,Morozov, Alexey S.,Karganova, Galina G.,Palyulin, Vladimir A.,Pentkovski, Vladimir M.,Zefirov, Nikolay S.
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supporting information
p. 869 - 874
(2013/10/01)
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