C2-symmetrical tetrahydroxyazepanes as inhibitors of glycosidases and HIV/FIV proteases.
C2-Symmetrical tetrahydroxyazepanes were synthesized as inhibitors for glycosidases. Tetrahydroxyazepane 1 is a non-specific inhibitor of various glycosidases, while compounds 2, 3 and 4 specifically inhibit beta-N-acetylglucosaminidase, beta-glucosidase, and alpha-fucosidase, respectively, with Ki in the micromolar range. Compound 1 is not an inhibitor of HIV/FIV proteases, but its 3,6-difluorobenzyl derivatives are moderate inhibitors of both enzymes.
Qian
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Department of Chemistry, Scripps Research Institute, La Jolla, CA 92037, USA.
Morís-Varas
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Fitzgerald
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Wong
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D016282:Aspartic Acid Endopeptidases / Q000037:antagonists & inhibitors*; D001381:Azepines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D017320:HIV Protease Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D050112:Imino Pyranoses; D008958:Models, Molecular; D010880:Piperidines / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
C105399:3,4,5,6-tetrahydroxyazepane; D001381:Azepines; D004791:Enzyme Inhibitors; D017320:HIV Protease Inhibitors; D050112:Imino Pyranoses; C105400:N-benzyl-3,4,5,6-tetrahydroxyazepane; D010880:Piperidines; C098432:isofagomine; D006026:Glycoside Hydrolases; D016282:Aspartic Acid Endopeptidases; C095555:FIV protease