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

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.

• Authors: 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
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 34 Issue 1 Pg. 392-7 (Jan 1991) ISSN: 0022-2623 [Print] United States
• PMID: 1671418 (Publication Type: Comparative Study, Journal Article)

Chemical References

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

Topics

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