SYNTHESIS OF CHIRAL AND ACHIRAL PYRANENAMINE DERIVATIVES - POTENT AGENTS WITH TOPICAL OCULAR ANTIALLERGIC ACTIVITY

被引:5
作者
GLUCHOWSKI, C
BISCHOFF, TE
GARST, ME
KAPLAN, LJ
DIETRICH, SW
ASWAD, AS
GAFFNEY, MA
AOKI, KR
GARCIA, C
WHEELER, LA
机构
[1] ALLERGAN PHARMACEUT INC,DEPT CHEM,IRVINE,CA 92715
[2] ALLERGAN PHARMACEUT INC,DEPT BIOL SCI,IRVINE,CA 92715
关键词
D O I
10.1021/jm00105a060
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The SS, RR and meso stereoisomers of pyranenamine SK&F 84210 (2) were synthesized stereospecifically starting from commercially available (R)-(-)- or (S)-(+)-2,2-dimethyl-1,3,dioxolane-4-methanol (3). 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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收藏
页码:392 / 397
页数:6
相关论文
共 16 条
[1]   OCULAR ALLERGY AND MAST-CELL STABILIZERS [J].
ALLANSMITH, MR ;
ROSS, RN .
SURVEY OF OPHTHALMOLOGY, 1986, 30 (04) :229-244
[2]   APPLICATION OF QUANTITATIVE STRUCTURE-ACTIVITY-RELATIONSHIPS IN THE DEVELOPMENT OF THE ANTI-ALLERGIC PYRANENAMINES [J].
CRAMER, RD ;
SNADER, KM ;
WILLIS, CR ;
CHAKRIN, LW ;
THOMAS, J ;
SUTTON, BM .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (06) :714-725
[3]  
CRAMER RD, 1980, ACS SYM SER, V118, P159
[5]  
Goen T M, 1986, J Am Optom Assoc, V57, P526
[6]   PASSIVE ANAPHYLAXIS IN RAT CONJUNCTIVA AND TOPICAL EFFECTS OF ANTI-ALLERGIC AGENTS - HYPERSENSITIVITY IN CONJUNCTIVA AND DRUG EFFICACY [J].
ISO, T ;
NAKAJIMA, N ;
SUDA, H ;
YAMAUCHI, H ;
UDA, K .
OPHTHALMIC RESEARCH, 1980, 12 (01) :9-15
[7]   CROMOLYN SODIUM IN SEASONAL ALLERGIC CONJUNCTIVITIS [J].
KRAY, KT ;
SQUIRE, EN ;
TIPTON, WR ;
SELNER, JC ;
ODEA, J ;
NELSON, HS .
JOURNAL OF ALLERGY AND CLINICAL IMMUNOLOGY, 1985, 76 (04) :623-627
[8]  
SCHWARTZ LB, 1987, ANN ALLERGY, V58, P226
[9]  
SKIDMORE IA, 1987, ISI ATLAS-PHARMACOL, P154
[10]   PYRANENAMINES - NEW SERIES OF ANTI-ALLERGIC COMPOUNDS [J].
SNADER, KM ;
CHAKRIN, LW ;
CRAMER, RD ;
GELERNT, YM ;
MIAO, CK ;
SHAH, DH ;
VENSLAVSKY, JW ;
WILLIS, CR ;
SUTTON, BM .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (06) :706-714