Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antibiotics, Antineoplastic / chemical synthesis
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Antibiotics, Antineoplastic / chemistry*
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Antibiotics, Antineoplastic / pharmacology*
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Antibiotics, Antineoplastic / toxicity
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Borates
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Boric Acids / chemical synthesis
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Boric Acids / chemistry*
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Cell Line, Tumor
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Cell Proliferation / drug effects
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Diazonium Compounds / chemical synthesis
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Diazonium Compounds / chemistry*
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Humans
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Microbial Sensitivity Tests
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Molecular Structure
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Olivomycins / chemical synthesis
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Olivomycins / chemistry*
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Olivomycins / pharmacology*
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Olivomycins / toxicity
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Viruses / drug effects
Substances
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Antibiotics, Antineoplastic
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Borates
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Boric Acids
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Diazonium Compounds
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Olivomycins
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fluoroboric acid