title: Design, synthesis and biological activity of carbohydrate-containing peptidomimetics as new ligands for the human tachykinin NK-2 receptor.
abstract: Enantiopure cycloadducts between glycals and alkyl or aryl heterodienes were selected as small, rigid, nonpeptide molecules able to superimpose to the structure of the cyclopeptide tachykinin NK-2 antagonist 1. The presence of three aromatic groups in the pyranose ring resulted essential for NK-2 affinity, while an increase in activity was shown by the corresponding sulfoxides.
authors.affiliation: Dipartimento di Chimica Organica Ugo Schiff, Universita' di Firenze, via della Lastruccia, 13, I-50019 Sesto Fiorentino, Florence, Italy.
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Capozzi
authors.forename: Sabrina
authors.initials: S
authors.lastname: Giannini
authors.forename: Stefano
authors.initials: S
authors.lastname: Menichetti
authors.forename: Cristina
authors.initials: C
authors.lastname: Nativi
authors.forename: Alessandro
authors.initials: A
authors.lastname: Giolitti
authors.forename: Riccardo
authors.initials: R
authors.lastname: Patacchini
authors.forename: Enzo
authors.initials: E
authors.lastname: Perrotta
authors.forename: Maria
authors.initials: M
authors.lastname: Altamura
authors.forename: Carlo
authors.initials: C
authors.lastname: Alberto Maggi
mesh_terms: D000818:Animals; D016466:CHO Cells; D006224:Cricetinae; D015195:Drug Design; D006801:Humans; D008024:Ligands; D008958:Models, Molecular; D018716:Molecular Mimicry; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000494:pharmacology; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000494:pharmacology; D018041:Receptors, Neurokinin-2 / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship; D013440:Sulfides; D013450:Sulfones; D014162:Transfection
chemical_list: D008024:Ligands; D009005:Monosaccharides; D009842:Oligopeptides; D010456:Peptides, Cyclic; D018041:Receptors, Neurokinin-2; D013440:Sulfides; D013450:Sulfones