136000-03-8Relevant academic research and scientific papers
The first general synthesis of 2-C-(β-d-glycopyranosyl)pyrimidines and their evaluation as inhibitors of some glycoenzymes
Szennyes, Eszter,Bokor, Eva,Langer, Peter,Gyémánt, Gy?ngyi,Docsa, Tibor,Sipos, ádám,Somsák, László
, p. 17439 - 17446 (2018/11/01)
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.
(β-D-ribofuranosyl)formamidine in the design and synthesis of 2-(β-D-ribofuranosyl)pyrimidines, including RF-containing derivatives
Iaroshenko, Viktor O.,Dudkin, Sergii,Sosnovskikh, Vyacheslav Ya.,Villinger, Alexander,Langer, Peter
supporting information, p. 3166 - 3173 (2013/06/27)
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
Regioselective synthesis of (trifluoromethyl)-β-chloroenones
Alvernhe, Gerard,Bensadat, Abdelkader,Ghobsi, Abdelkader,Laurent, Andre,Laurent, Eliane
, p. 169 - 172 (2007/10/03)
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.
