title: Synthesis and antiallergy activity of 4-(diarylhydroxymethyl)-1-[3-(aryloxy)propyl]piperidines and structurally related compounds.
abstract: A series of 4-(diarylhydroxymethyl)-1-[3-(aryloxy)propyl]piperidines was synthesized and evaluated for antiallergy activity. Several analogues had potent activity in the passive foot anaphylaxis (PFA) assay, an IgE-mediated model useful in the detection of compounds possessing antiallergic activity. In particular 1-[4-[3-[4-[bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl] propoxy]-3-methoxyphenyl]ethanone (1, AHR-5333) was more potent than oxatomide and terfenadine in this assay.
authors.affiliation: Department of Chemical Research and Pharmacology, A.H. Robins Company, Richmond, Virginia 23261-6609.
authors.forename: D A
authors.initials: DA
authors.lastname: Walsh
authors.forename: S K
authors.initials: SK
authors.lastname: Franzyshen
authors.forename: J M
authors.initials: JM
authors.lastname: Yanni
mesh_terms: D000707:Anaphylaxis / Q000188:drug therapy; D000818:Animals; D001559:Benzhydryl Compounds / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D004353:Drug Evaluation, Preclinical; D006168:Guinea Pigs; D006967:Hypersensitivity / Q000188:drug therapy*; D008297:Male; D010323:Passive Cutaneous Anaphylaxis / Q000187:drug effects; D010879:Piperazines / Q000494:pharmacology; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology*; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship; D016593:Terfenadine
chemical_list: D001559:Benzhydryl Compounds; D010879:Piperazines; D010880:Piperidines; C055541:AHR 5333; D016593:Terfenadine; C015408:oxatomide