A proposal for the mechanism-of-action of diazoparaquinone natural products.
Treatment of the representative diazoparaquinone prekinamycin dimethyl ether with Bu3SnH/AIBN in aromatic solvents furnishes moderate-to-good yields of formal aryl adducts wherein a molecule of solvent is attached to the carbon (C(11)) previously bearing the diazo function. Substituent studies provide evidence in support of a radical aromatic substitution mechanism, in which radical addition to the diazoparaquinone function generates an intermediate C(11) vinylic radical.
Feldman
Ken S
KS
Department of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA. ksf@chem.psu.edu
Eastman
Kyle J
KJ
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D004247:DNA / Q000737:chemistry; D004249:DNA Damage / Q000187:drug effects*; D011809:Quinones / Q000737:chemistry / Q000494:pharmacology*; D000095602:Angucyclines and Angucyclinones
D000900:Anti-Bacterial Agents; D004247:DNA; D011809:Quinones; C059018:pre-kinamycin; D000095602:Angucyclines and Angucyclinones