Synthesis and biological activity of some 1-N-substituted 2-acetamido-2-deoxy-β-d-glycopyranosylamine derivatives and related analogs
| Autor: | Brajeswar Paul, Ralph J. Bernacki, Walter Korytnyk |
|---|---|
| Rok vydání: | 1980 |
| Předmět: |
Glycoconjugate
Stereochemistry Cell Biochemistry Acetylglucosamine Analytical Chemistry Mice Structure-Activity Relationship medicine Animals Leukemia L1210 chemistry.chemical_classification Glucosamine Leukemia Experimental Organic Chemistry Mammary Neoplasms Experimental Biological activity General Medicine medicine.disease In vitro Leukemia medicine.anatomical_structure chemistry Acetylation Leucine Macromolecule |
| Zdroj: | Carbohydrate Research. 80:99-115 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/s0008-6215(00)85318-5 |
| Popis: | Several 1-N-substituted derivatives [haloacetyl-, glycyl-, (dimethyl)aminoacetyl-, azidoacetyl-, trifluoroacetyl-, and trifluoromethylsulfonyl-] of 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β- d -glucopyranosylamine (1) were synthesized as potential metabolic inhibitors of cellular-membrane glycoconjugates. Several fully acetylated derivatives were found to inhibit growth of mouse mammary adenocarcinoma TA3, leukemia L-1210, or leukemia P-288 cells at 1–0.01m M concentration in vitro. Some of these derivatives were less active after O-deacetylation. Analogs of 1 in which NH2-1 was replaced by OH- or OAc-1 were also active on the same cell systems. The growth-inhibitory activity was correlated with inhibition of the incorporation of 2-amino-deoxy- d -glucose and l -leucine into a macromolecular fraction. |
| Databáze: | OpenAIRE |
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