Reaction of the antitumor antibiotic olivomycin I with aryl diazonium salts. Synthesis, cytotoxic and antiretroviral potency of 5-aryldiazenyl-6-O-deglycosyl derivatives of olivomycin I
| Autor: | Jan Balzarini, Eugenyi E. Bykov, Maria N. Preobrazhenskaya, Eugenia N. Olsufyeva, Lyubov G. Dezhenkova, Alexander A. Shtil, Konstantin F. Turchin, Anna N. Tevyashova |
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| Rok vydání: | 2009 |
| Předmět: |
Stereochemistry
Clinical Biochemistry Pharmaceutical Science Microbial Sensitivity Tests Azo coupling Biochemistry Chemical synthesis chemistry.chemical_compound Electrophilic substitution Boric Acids Cell Line Tumor Borates Drug Discovery Animals Humans Molecular Biology Cell Proliferation chemistry.chemical_classification Antibiotics Antineoplastic Diazonium Compounds Azo compound Molecular Structure Aryl Organic Chemistry Combinatorial chemistry chemistry Viruses Proton NMR Molecular Medicine Olivomycin Olivomycins |
| Zdroj: | Bioorganic & Medicinal Chemistry. 17:4961-4967 |
| ISSN: | 0968-0896 |
| DOI: | 10.1016/j.bmc.2009.05.076 |
| Popis: | The azo coupling of the antibiotic olivomycin I (1) with aryl diazonium tetrafluoroborates produced 5-aryldiazenyl-6-O-deglycosyl derivatives of 1. The structures of new compounds were confirmed by (1)H NMR and mass spectrometry analysis. A quantum-chemical study was performed to analyze the possible directions of electrophilic substitution of 1 and the easiness of 6-O-disaccharide hydrolysis in the course of azo coupling. The antiproliferative and anti-retroviral activities of novel derivatives were studied. |
| Databáze: | OpenAIRE |
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