2. Academic Validation
  3. 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

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

  • Bioorg Med Chem. 2009 Jul 15;17(14):4961-7. doi: 10.1016/j.bmc.2009.05.076.
Anna N Tevyashova 1,  Eugenia N Olsufyeva,  Konstantin F Turchin,  Jan Balzarini,  Eugenyi E Bykov,  Lyubov G Dezhenkova,  Alexander A Shtil,  Maria N Preobrazhenskaya
Affiliations

Affiliation

  • 1 Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, 11 B. Pirogovskaya, Moscow 119021, Russian Federation.
PMID: 19535252 DOI: 10.1016/j.bmc.2009.05.076
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.

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