Simplified dynemicin analogues: diastereoselective synthesis and evaluation of their activity against plasmid DNA.
The total synthesis of two diastereoisomeric simplified dynemicin analogues is reported. The key steps involved are: the regio- and diastereoselective functionalisation of an appropriate racemic quinoline precursor and the ring closure to give the 10-membered enediyne moiety through a Pd(0)-catalysed Stille reaction. After the successful conversion of one of these derivatives into a compound more readily activable under nearly physiological conditions, the activity against plasmid DNA was evaluated.
Guanti
Giuseppe
G
Dipartimento di Chimica e Chimica Industriale, via Dodecaneso 31, 16146 Genova, Italy. guanti@chimica.unige.it
Riva
Renta
R
D000880:Anthraquinones / Q000138:chemical synthesis* / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D053281:Enediynes; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D010957:Plasmids / Q000378:metabolism*; D011804:Quinolines / Q000737:chemistry; D013237:Stereoisomerism
D000880:Anthraquinones; D000900:Anti-Bacterial Agents; D053281:Enediynes; D011804:Quinolines; D004247:DNA; C061229:dynemicin A