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.
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.
Tevyashova
Anna N
AN
Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, 11 B. Pirogovskaya, Moscow 119021, Russian Federation.
Olsufyeva
Eugenia N
EN
Turchin
Konstantin F
KF
Balzarini
Jan
J
Bykov
Eugenyi E
EE
Dezhenkova
Lyubov G
LG
Shtil
Alexander A
AA
Preobrazhenskaya
Maria N
MN
D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D001881:Borates; D001888:Boric Acids / Q000138:chemical synthesis / Q000737:chemistry*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003979:Diazonium Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009848:Olivomycins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000633:toxicity; D014780:Viruses / Q000187:drug effects
D000903:Antibiotics, Antineoplastic; D001881:Borates; D001888:Boric Acids; D003979:Diazonium Compounds; D009848:Olivomycins; C098759:fluoroboric acid