S-, N-, and O-glycosyl derivatives of 2-acetamido-2-deoxy-d-glucose with hydrophobic aglycons as potential chemotherapeutic agents and N-acetyl-β-d-glucosaminidase inhibitors
| Autor: | Brajeswar Paul, Walter Korytnyk |
|---|---|
| Rok vydání: | 1984 |
| Předmět: |
Magnetic Resonance Spectroscopy
Optical Rotation Spectrophotometry Infrared Stereochemistry Antineoplastic Agents Adenocarcinoma Biochemistry Analytical Chemistry Acylation Mice Structure-Activity Relationship chemistry.chemical_compound Acetylglucosaminidase Animals Structure–activity relationship Glycosyl biology 2-Acetamido-2-Deoxy-D-Glucose Organic Chemistry Aminoglycoside Mammary Neoplasms Experimental General Medicine Nuclear magnetic resonance spectroscopy In vitro carbohydrates (lipids) Hexosaminidases Liver chemistry Enzyme inhibitor biology.protein Cattle Female Indicators and Reagents |
| Zdroj: | Carbohydrate Research. 126:27-43 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/0008-6215(84)85124-1 |
| Popis: | S-, N-, and O-Glycosyl derivatives of 2-acetamido-2-deoxy-D-glucose with hydrophobic aglycons have been obtained as potential, plasma-membrane active agents. 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-beta-D-glucopyranose (6) was converted into benzyl, diphenylmethyl, triphenylmethyl, and other thioglycosides. Acylation of 6 gave adamantoyl and haloacetyl derivatives. A similar series of N- and O-glycosyl derivatives was obtained from the corresponding NH2-1 and OH-1 analogs of 6, such as O- and N-dinitrophenyl, O- and N-adamantoyl, and N-4-methylbenzylidene derivatives. Several N- and S-glycosyl derivatives were found to inhibit mouse mammary adenocarcinoma (TA3) cells in vitro as well as N-acetyl-beta-D-glucosaminidase from beef liver. |
| Databáze: | OpenAIRE |
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