Synthesis and antiallergy activity of 4-(diarylhydroxymethyl)-1-[3-(aryloxy)propyl]piperidines and structurally related compounds.
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.
Walsh
D A
DA
Department of Chemical Research and Pharmacology, A.H. Robins Company, Richmond, Virginia 23261-6609.
Franzyshen
S K
SK
Yanni
J M
JM
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
D001559:Benzhydryl Compounds; D010879:Piperazines; D010880:Piperidines; C055541:AHR 5333; D016593:Terfenadine; C015408:oxatomide