Nine of 16 stereoisomeric polyhydroxylated proline amides are potent β-N-acetylhexosaminidase inhibitors

Journal of Organic Chemistry

Volumn 79, Issue 8, 2014, Pages 3398-3409

  Ayers, Benjamin J ^a   Glawar, Andreas F G ^a,b   Martínez, R Fernando ^a   Ngo, Nigel ^a   Liu, Zilei ^a   Fleet, George W J ^a   Butters, Terry D ^b   Nash, Robert J ^c   Yu, Chu Yi ^d   Wormald, Mark R ^b   Nakagawa, Shinpei ^e   Adachi, Isao ^e   Kato, Atsushi ^e   Jenkinson, Sarah F ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF OXFORD   (United Kingdom)

^c Phytoquest Limited   (United Kingdom)

^d INSTITUTE OF CHEMISTRY   (China)

^e UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC COMPOUNDS; STEREOCHEMISTRY;

AZETIDINES; N-ACETYLHEXOSAMINIDASE; POLYHYDROXYLATED; STRUCTURAL CORRELATION;

AMIDES;

5 ACETAMIDO 1 O ACETYL 2 N,3 O DIBENZYL 2,4,5 TRIDEOXY 2,4 IMINO DEXTRO RIBITOL; 5 ACETAMIDO 2 N,3 O DIBENZYL 2,4,5 TRIDEOXY 2,4 IMINO DEXTRO RIBITOL; 5 ACETAMIDO 2,4,5 TRIDEOXY 2,4 IMINO DEXTRO RIBITOL HYDROCHLORIDE; AMIDE; AZETIDINE ACETAMIDE; BETA N ACETYLHEXOSAMINIDASE INHIBITOR; ENZYME INHIBITOR; METHYL 2 N (TERT BUTOXYCARBONYL) 3,6 DI O BENZYL 2,5 DIDEOXY 2,5 IMINO LEVO GULONAMIDE; METHYL 2 N (TERT BUTOXYCARBONYL) 3,6 DI O BENZYL 2,5 DIDEOXY 2,5 IMINO LEVO IDONAMIDE; METHYL 2 N,3 O DIBENZYL 2,4 DIDEOXY 2,4 IMINO 5 O METHANESULFONYL DEXTRO RIBONATE; METHYL 2,5 DIDEOXY 2,5 IMINO DEXTRO ALLONAMIDE; METHYL 2,5 DIDEOXY 2,5 IMINO DEXTRO ALTRONAMIDE; METHYL 2,5 DIDEOXY 2,5 IMINO DEXTRO GLUCONAMIDE; METHYL 2,5 DIDEOXY 2,5 IMINO DEXTRO MANNONAMIDE; METHYL 2,5 DIDEOXY 2,5 IMINO LEVO GALACTONAMIDE; METHYL 2,5 DIDEOXY 2,5 IMINO LEVO GULONAMIDE; METHYL 2,5 DIDEOXY 2,5 IMINO LEVO IDONAMIDE; METHYL 2,5 DIDEOXY 2,5 IMINO LEVO TALONAMIDE; METHYL 5 AZIDO 2 N,3 O DIBENZYL 2,4,5 TRIDEOXY 2,4 IMINO DEXTRO RIBONATE; METHYL 5 AZIDO 3,6 DI O BENZYL 5 DEOXY 2 O METHANESULFONYL DEXTRO ALLONAMIDE; METHYL 5 AZIDO 3,6 DI O BENZYL 5 DEOXY 2 O METHANESULFONYL DEXTRO ALTRONAMIDE; METHYL 5 AZIDO 3,6 DI O BENZYL 5 DEOXY 2 O METHANESULFONYL DEXTRO MANNONAMIDE; METHYL 5 AZIDO 3,6 DI O BENZYL 5 DEOXY 2 O METHANESULFONYL LEVO GALACTONAMIDE; METHYL 5 AZIDO 3,6 DI O BENZYL 5 DEOXY 2 O METHANESULFONYL LEVO GULONAMIDE; METHYL 5 AZIDO 3,6 DI O BENZYL 5 DEOXY 2 O METHANESULFONYL LEVO IDONAMIDE; METHYL 5 AZIDO 3,6 DI O BENZYL 5 DEOXY 2 O METHANESULFONYL LEVO TALONAMIDE; N METHYL 5 (HYDROXYMETHYL) 3,4 DIHYDROXYPROLINE AMIDE; PROLINE; UNCLASSIFIED DRUG;

AMINOLYSIS; ARTICLE; DRUG SYNTHESIS; ENANTIOMER; EPIMERIZATION; ESTERIFICATION; HUMAN; HUMAN CELL; HYDROGENATION; IC 50; IN VITRO STUDY; RING OPENING; STEREOCHEMISTRY; STEREOISOMERISM;

ACETAMIDES; AMIDES; AZETIDINECARBOXYLIC ACID; BETA-N-ACETYLHEXOSAMINIDASES; KINETICS; PROLINE; STEREOISOMERISM;

EID: 84898967445     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500157p     Document Type: Article

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