Synthesis of chiral and achiral pyranenamine derivatives. Potent agents with topical ocular antiallergic activity

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 a...

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Veröffentlicht in:	Journal of medicinal chemistry 1991-01, Vol.34 (1), p.392-397
Hauptverfasser:	Gluchowski, Charles, Bischoff, Trudy E, Garst, Michael E, Kaplan, Lester J, Dietrich, Steven W, Aswad, Angelika S, Gaffney, Mary A, Aoki, K. Roger, Garcia, Carlos, Wheeler, Larry A
Format:	Artikel
Sprache:	eng
Schlagworte:	Anaphylaxis - drug therapy Aniline Compounds - chemical synthesis Aniline Compounds - therapeutic use Animals Chemistry Exact sciences and technology Eye Diseases - drug therapy Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Histamine H1 Antagonists - chemical synthesis Indicators and Reagents Molecular Structure Organic chemistry Preparations and properties Pyrones - chemical synthesis Pyrones - therapeutic use Rats Stereoisomerism Structure-Activity Relationship
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Zusammenfassung:	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.
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm00105a060