title: Synthesis and pharmacological evaluation of the individual stereoisomers of 3-[methyl(1,2,3,4-tetrahydro-2-naphthalenyl)amino]-1-indanone, a potent mast cell stabilising agent.
abstract: Each stereoisomer of 3-[methyl(1,2,3,4-tetrahydro-2-naphthalenyl)amino]-1-indanone, 1a-d, was prepared and evaluated in vitro for its ability to prevent mediator release induced by different degranulating agents from rodent mast cells and also in vivo against passive cutaneous anaphylaxis. The manner in which the stereoisomers prevented direct membrane activation was found to be highly dependent on the stereochemistry of the individual isomers. Stereoisomer 1b was the most active isomer in vivo, exhibiting superior activity to disodium cromoglycate.
authors.affiliation: School of Pharmacy and Pharmaceutical Sciences, University of Dublin, Trinity College, Dublin 2, Ireland.
authors.forename: Adam J
authors.initials: AJ
authors.lastname: Byrne
authors.forename: James W
authors.initials: JW
authors.lastname: Barlow
authors.forename: John J
authors.initials: JJ
authors.lastname: Walsh
mesh_terms: D015081:2-Naphthylamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D018360:Crystallography, X-Ray; D006632:Histamine / Q000378:metabolism; D007189:Indans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008407:Mast Cells / Q000187:drug effects*; D051379:Mice; D008968:Molecular Conformation; D010323:Passive Cutaneous Anaphylaxis / Q000187:drug effects; D013237:Stereoisomerism; D013552:Swine
chemical_list: C558291:3-(methyl(1,2,3,4-tetrahydro-2-naphthalenyl)amino)-1-indanone; D007189:Indans; D006632:Histamine; D015081:2-Naphthylamine