- The first general synthesis of 2-C-(β-d-glycopyranosyl)pyrimidines and their evaluation as inhibitors of some glycoenzymes
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A systematic study was performed on the preparation of unknown 2-C-(β-d-glucopyranosyl)pyrimidines. Pinner type cyclisation of O-perbenzylated C-(β-d-glucopyranosyl)formamidine with β-ketoesters, dimethyl malonate, and β-diketone derived α,β-unsaturated β-chloroketones followed by catalytic hydrogenation resulted in various substituted 2-C-(β-d-glucopyranosyl)-pyrimidin-4(3H)-ones, and 2-C-(β-d-glucopyranosyl)-4,6-disubstituted-pyrimidines, respectively, in moderate to good yields. The above pyrimidine derivatives were also obtained by ring closure of the unprotected C-(β-d-glucopyranosyl)formamidine with the same 1,3-dielectrophiles. In addition, a continuous one-pot three-step procedure starting from O-peracylated d-glycopyranosyl cyanides was also elaborated to give representatives of the aforementioned pyrimidines with various sugar configurations in acceptable to excellent overall yields (25-94%). Due to the versatility of the applied 1,3-dielectrophiles, these synthetic routes represent the first expansible method to obtain the target compounds. The new C-glycopyranosyl pyrimidines showed moderate inhibition against α-glucosidase and β-galactosidase enzymes, had, however, no activity against glycogen phosphorylase. The obtained molecule library is ready for further biological testing.
- Szennyes, Eszter,Bokor, Eva,Langer, Peter,Gyémánt, Gy?ngyi,Docsa, Tibor,Sipos, ádám,Somsák, László
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- (β-D-ribofuranosyl)formamidine in the design and synthesis of 2-(β-D-ribofuranosyl)pyrimidines, including RF-containing derivatives
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A wide range of novel 2-(β-D-ribofuranosyl)pyrimidines, including RF-containing derivatives, have been synthesized by the reaction of (β-D-ribofuranosyl)formamidine with various dielectrophilic substrates such as 3-alkoxy- and 3-chloro-1-(polyf
- Iaroshenko, Viktor O.,Dudkin, Sergii,Sosnovskikh, Vyacheslav Ya.,Villinger, Alexander,Langer, Peter
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supporting information
p. 3166 - 3173
(2013/06/27)
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- Regioselective synthesis of (trifluoromethyl)-β-chloroenones
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The regioselectivity of the conversion of 1,3-diketones into β-chloroenones can be changed by the appropriate choice of the reagent: reaction with "Vilsmeier's reagent" prepared from POCl3 and dimethylformamide or treatment of the diketone with the oxalyl chloride in the presence of dimethylformamide.
- Alvernhe, Gerard,Bensadat, Abdelkader,Ghobsi, Abdelkader,Laurent, Andre,Laurent, Eliane
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p. 169 - 172
(2007/10/03)
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- Synthesis of γγγ-trifluorocarbonyl compounds
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γγγ-Trifluorocarbonyl compounds are easily obtained in a good yield by introduction of the 1,1,1-trifluoroethyl moiety (CF3-CH2-) on the α-methylene group of a ketone.
- Laurent,Lesniak
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p. 8091 - 8092
(2007/10/02)
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