title: Alpha2-adrenoreceptors profile modulation. 3.1 (R)-(+)-m-nitrobiphenyline, a new efficient and alpha2C-subtype selective agonist.
abstract: To assess the stereochemical requirements for efficient alpha2C-adrenoreceptor activation, the enantiomeric forms of m-nitrobiphenyline [(+/-)-5] were prepared and tested on cells expressing the human alpha2-adrenoreceptor subtypes. The importance of chirality was confirmed, since the enantiomer (R)-(+)-5 was much more efficient than (S)-(-)-5 in producing alpha2C-activation. Surprising reversal of enantioselectivity was observed with respect to structurally similar biphenyline [(+/-)-1] whose (S)-(-)-form proved the preferred alpha2C-configuration.
authors.affiliation: Dipartimento di Scienze Chimiche, Università degli Studi di Camerino, Via S. Agostino 1, 62032 Camerino, Italy.
authors.forename: Pierre-Antoine
authors.initials: PA
authors.lastname: Crassous
authors.forename: Claudia
authors.initials: C
authors.lastname: Cardinaletti
authors.forename: Antonio
authors.initials: A
authors.lastname: Carrieri
authors.forename: Bruno
authors.initials: B
authors.lastname: Bruni
authors.forename: Massimo
authors.initials: M
authors.lastname: Di Vaira
authors.forename: Francesco
authors.initials: F
authors.lastname: Gentili
authors.forename: Francesca
authors.initials: F
authors.lastname: Ghelfi
authors.forename: Mario
authors.initials: M
authors.lastname: Giannella
authors.forename: Hervé
authors.initials: H
authors.lastname: Paris
authors.forename: Alessandro
authors.initials: A
authors.lastname: Piergentili
authors.forename: Wilma
authors.initials: W
authors.lastname: Quaglia
authors.forename: Stéphane
authors.initials: S
authors.lastname: Schaak
authors.forename: Cristian
authors.initials: C
authors.lastname: Vesprini
authors.forename: Maria
authors.initials: M
authors.lastname: Pigini
mesh_terms: D058647:Adrenergic alpha-2 Receptor Agonists; D000818:Animals; D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016466:CHO Cells; D006224:Cricetinae; D003412:Cricetulus; D000242:Cyclic AMP / Q000096:biosynthesis; D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011869:Radioligand Assay; D013237:Stereoisomerism
chemical_list: C524114:3-nitrobiphenyline; D058647:Adrenergic alpha-2 Receptor Agonists; D001713:Biphenyl Compounds; D007093:Imidazoles; D000242:Cyclic AMP