title: Synthesis of chiral and achiral pyranenamine derivatives. Potent agents with topical ocular antiallergic activity.
abstract: The SS, RR and meso stereoisomers of pyranenamine SK&F 84210 were synthesized stereospecifically starting from commercially available (R)-(-)- or (S)-(+)-2,2-dimethyl-1,3-dioxolane-4-methanol. In addition, two achiral pyranenamines 19 and 26 were also synthesized. When evaluated by intravenous and topical routes in the rat passive ocular anaphylaxis (POA) assay, (SS)- and meso-2 as well as achiral compounds 19 and 26 were found to be more potent antiallergic agents than (RR)-2.
authors.affiliation: Department of Chemical Sciences, Incorporated, Irvine, California 92715-1599.
authors.forename: C
authors.initials: C
authors.lastname: Gluchowski
authors.forename: T E
authors.initials: TE
authors.lastname: Bischoff
authors.forename: M E
authors.initials: ME
authors.lastname: Garst
authors.forename: L J
authors.initials: LJ
authors.lastname: Kaplan
authors.forename: S W
authors.initials: SW
authors.lastname: Dietrich
authors.forename: A S
authors.initials: AS
authors.lastname: Aswad
authors.forename: M A
authors.initials: MA
authors.lastname: Gaffney
authors.forename: K R
authors.initials: KR
authors.lastname: Aoki
authors.forename: C
authors.initials: C
authors.lastname: Garcia
authors.forename: L A
authors.initials: LA
authors.lastname: Wheeler
mesh_terms: D000707:Anaphylaxis / Q000188:drug therapy*; D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000627:therapeutic use; D000818:Animals; D005128:Eye Diseases / Q000188:drug therapy*; D006634:Histamine H1 Antagonists / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000627:therapeutic use; D051381:Rats; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000814:Aniline Compounds; D006634:Histamine H1 Antagonists; D007202:Indicators and Reagents; D011753:Pyrones; C067217:SK&F 84210