Efficient inhibition of muscle and liver glycogen phosphorylases by a new glucopyranosylidene-spiro-thiohydantoin
Reaction of C-(1-bromo-1-deoxy-β-D-glucopyranosyl)formamide 2 with thiocyanate ions was the key step of a short synthesis of D- glucopyranosylidene-spiro-thiohydantoin 7 which proved to be a potent inhibitor of muscle and liver glycogen phosphorylases.
Osz, Erzsebet,Somsak, Laszlo,Szilagyi, Laszlo,Kovacs, Laszlo,Docsa, Tibor,Toth, Bela,Gergely, Pal
Anomeric spirocycles by solvent incorporation: Reactions of O-peracylated (glyculopyranose and glyculopyranosyl bromide)onamide derivatives with ketones
Reactions of O-peracetylated (α-d-galacto-heptulopyranosyl bromide)onamide and O-perbenzoylated (α-d-gluco-heptulopyranosyl bromide)onamide with ketones in the presence of silver(I) salt promoters gave the corresponding O-peracylated 1′,5′-anhydro-d-glyci
Phi, Andrs,Czifrk, Katalin,K?vr, Katalin E.,Somsk, Lszl
Ritter-type reaction of C-(1-bromo-1-deoxy-d-glycopyranosyl)formamides and its application for the synthesis of oligopeptides incorporating anomeric α-amino acids
O-Peracetylated or -perbenzoylated C-(1-bromo-1-deoxy-d-glycopyranosyl) formamides of d-gluco, d-galacto, and d-arabino configuration were reacted with Ag(I)-salts or HgO in nitrile solvents to give N-acyl-1-cyano-d- glycopyranosylamines with an axial C-N
Czifrák, Katalin,Gyóllai, Viktor,K?vér, Katalin E.,Somsák, László
scheme or table
p. 2104 - 2112
(2011/11/06)
Synthesis of some O-, S- and N-glycosides of hept-2-ulopyranosonamides
(O-Peracylated α-d-gluco- and -galacto-hept-2-ulopyranosylbromide)onamides gave the corresponding (alkyl β-d-glyco-hept-2-ulopyranoside)onamides under Koenigs-Knorr conditions, and similar aryl glycosides were obtained with sodium phenolates; (aryl and he
Nagy, Veronika,Czifrak, Katalin,Benyei, Attila,Somsak, Laszlo
experimental part
p. 921 - 927
(2009/08/07)
Synthesis of and a comparative study on the inhibition of muscle and liver glycogen phosphorylases by epimeric pairs of D-gluco- and D-xylopyranosylidene-spiro-(thio)hydantoins and N-(D-glucopyranosyl) amides
D-Gluco- and D-xylopyranosylidene-spiro-hydantoins and -thiohydantoins were prepared from the parent sugars in a six-step, highly chemo-, regio-, and stereoselective procedure. In the key step of the syntheses C-(1-bromo-1-deoxy-β-D-glycopyranosyl)formami
Novel glycosylidene-spiro-heterocycles from unprecedented solvent incorporation in Koenigs-Knorr-like reactions of C-(1-bromo-1-deoxy-β-D-glycopyranosyl)formamides
The title compounds give glycopyranosylidene-spiro-dioxolanes 3 and 4 in acetone and C-(1-methylsulfanylmethoxy-α-D-glycopyranosyl)formamides 5 in DMSO in the presence of Ag2CO3 and AgF, respectively.
A straightforward route to hydantocidin analogues with pyranose ring structure
Partial hydrolysis of the nitrile moiety in aeetylated 1-bromo-glycopyranosyl cyanides 1 and 9 mediated by TiCl4 gave C-(1-bromo-1-deoxy-glycopyranosyl) formamides 2 and 10 whose reaction either with AgOCN, AgSCN or KSCN in nitromethane resulted in the formation of glycopyranosylidene-spirohydantoins 3, 11 and 15 and -thiohydantoins 7 and 16. Zemplen-deacetylation gave the pyranoid epihydantocidin analogues 4 and 12, and thiohydantocidin analogues 8 and 17, respectively.