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

C Gluchowski; T E Bischoff; M E Garst; L J Kaplan; S W Dietrich; A S Aswad; M A Gaffney; K R Aoki; C Garcia; L A Wheeler

doi:10.1021/jm00105a060

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

J Med Chem. 1991 Jan;34(1):392-7. doi: 10.1021/jm00105a060.

Authors

C Gluchowski¹, T E Bischoff, M E Garst, L J Kaplan, S W Dietrich, A S Aswad, M A Gaffney, K R Aoki, C Garcia, L A Wheeler

Affiliation

¹ Department of Chemical Sciences, Incorporated, Irvine, California 92715-1599.

PMID: 1671418
DOI: 10.1021/jm00105a060

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.

Publication types

Comparative Study

MeSH terms

Anaphylaxis / drug therapy*
Aniline Compounds / chemical synthesis*
Aniline Compounds / therapeutic use
Animals
Eye Diseases / drug therapy*
Histamine H1 Antagonists / chemical synthesis*
Indicators and Reagents
Molecular Structure
Pyrones / chemical synthesis*
Pyrones / therapeutic use
Rats
Stereoisomerism
Structure-Activity Relationship

Substances

Aniline Compounds
Histamine H1 Antagonists
Indicators and Reagents
Pyrones
SK&F 84210