868960-50-3Relevant academic research and scientific papers
Glucopyranosylidene-spiro-imidazolinones, a New Ring System: Synthesis and Evaluation as Glycogen Phosphorylase Inhibitors by Enzyme Kinetics and X-ray Crystallography
Szabó, Katalin E.,Kyriakis, Efthimios,Psarra, Anna-Maria G.,Karra, Aikaterini G.,Sipos, ádám,Docsa, Tibor,Stravodimos, George A.,Katsidou, Elisabeth,Skamnaki, Vassiliki T.,Liggri, Panagiota G. V.,Zographos, Spyros E.,Mándi, Attila,Király, Sándor Balázs,Kurtán, Tibor,Leonidas, Demetres D.,Somsák, László
supporting information, p. 6116 - 6136 (2019/08/02)
Epimeric series of aryl-substituted glucopyranosylidene-spiro-imidazolinones, an unprecedented new ring system, were synthesized from the corresponding Schiff bases of O-perbenzoylated (gluculopyranosylamine)onamides by intramolecular ring closure of the aldimine moieties with the carboxamide group elicited by N-bromosuccinimide in pyridine. Test compounds were obtained by Zemplén O-debenzoylation. Stereochemistry and ring tautomers of the new compounds were investigated by NMR, time-dependent density functional theory (TDDFT)-electronic circular dichroism, and DFT-NMR methods. Kinetic studies with rabbit muscle and human liver glycogen phosphorylases showed that the (R)-imidazolinones were 14-216 times more potent than the (S) epimers. The 2-naphthyl-substituted (R)-imidazolinone was the best inhibitor of the human enzyme (Ki 1.7 μM) and also acted on HepG2 cells (IC50 177 μM). X-ray crystallography revealed that only the (R) epimers bound in the crystal. Their inhibitory efficacy is based on the hydrogen-bonding interactions of the carbonyl oxygen and the NH of the imidazolinone ring.
Synthesis of some derivatives of C-(1-deoxy-1-N-substituted-d- glucopyranosyl)formic acid (D-gluco-hept-2-ulopyranosonic acid) as potential inhibitors of glycogen phosphorylase
Czifrak, Katalin,Kovacs, Laszlo,Koever, Katalin E.,Somsak, Laszlo
, p. 2328 - 2334 (2007/10/03)
Per-O-benzoylated derivatives (amide, methyl ester and glycinamide) of C-(1-azido-1-deoxy-α-d-glucopyranosyl)formic acid obtained by azide substitution in the corresponding C-(1-bromo-1-deoxy-β-d-glucopyranosyl) formic acid derivatives were debenzoylated
