title: A simple synthesis of N-perfluoroacylated and N-acylated glycals of neuraminic acid with a cyclic aminic substituent at the 4α position as possible inhibitors of sialidases.
abstract: A simple protocol for the synthesis of N-perfluoroacylated and N-acylated glycals of neuraminic acid, with a secondary cyclic amine (morpholine or piperidine) at the 4α position, has been set-up, starting from peracetylated N-acetylneuraminic acid methyl ester that undergoes, sequentially to its direct N-transacylation followed by a C-4 amination, a β-elimination, and a selective hydrolysis of the ester functions, without affecting the sensitive perfluorinated amide.
authors.affiliation: Department of Chemistry, Biochemistry and Biotechnology for the Medicine, Via Saldini 50, Milano, Italy. paola.rota@unimi.it
authors.forename: Paola
authors.initials: P
authors.lastname: Rota
authors.forename: Pietro
authors.initials: P
authors.lastname: Allevi
authors.forename: Irene S
authors.initials: IS
authors.lastname: Agnolin
authors.forename: Roberto
authors.initials: R
authors.lastname: Mattina
authors.forename: Nadia
authors.initials: N
authors.lastname: Papini
authors.forename: Mario
authors.initials: M
authors.lastname: Anastasia
mesh_terms: D000215:Acylation; D000588:Amines / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000494:pharmacology; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D004986:Ether / Q000737:chemistry*; D017611:Fluorine Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D009438:Neuraminic Acids / Q000737:chemistry*; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship; D014734:Vibrio cholerae / Q000187:drug effects / Q000201:enzymology
chemical_list: D000588:Amines; D002241:Carbohydrates; D004791:Enzyme Inhibitors; D017611:Fluorine Compounds; D009438:Neuraminic Acids; D004986:Ether; D009439:Neuraminidase