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 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.
Gluchowski
C
C
Department of Chemical Sciences, Incorporated, Irvine, California 92715-1599.
Bischoff
T E
TE
Garst
M E
ME
Kaplan
L J
LJ
Dietrich
S W
SW
Aswad
A S
AS
Gaffney
M A
MA
Aoki
K R
KR
Garcia
C
C
Wheeler
L A
LA
D000707:Anaphylaxis / Q000188:drug therapy*; D000814:Aniline Compounds / Q000138:chemical synthesis* / Q000627:therapeutic use; D000818:Animals; D005128:Eye Diseases / Q000188:drug therapy*; D006634:Histamine H1 Antagonists / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000627:therapeutic use; D051381:Rats; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000814:Aniline Compounds; D006634:Histamine H1 Antagonists; D007202:Indicators and Reagents; D011753:Pyrones; C067217:SK&F 84210