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  • Title: Synthesis of chiral and achiral pyranenamine derivatives. Potent agents with topical ocular antiallergic activity.
    Author: Gluchowski C, Bischoff TE, Garst ME, Kaplan LJ, Dietrich SW, Aswad AS, Gaffney MA, Aoki KR, Garcia C, Wheeler LA.
    Journal: J Med Chem; 1991 Jan; 34(1):392-7. PubMed ID: 1671418.
    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.
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