title: Synthesis and reactivity of cinnoline-fused cyclic enediyne.
abstract: A short and efficient synthesis of cinnoline-fused cyclic enediyne is reported. Richter cyclization of o-(1,3-butadiynyl)phenyltriazene produced 3-alkynyl-4-bromocinnoline. The Sonogashira coupling of the latter with 5-hexyn-1-ol was employed for the introduction of a second acetylenic moiety. The crucial cyclization step was achieved under Nozaki-Hiyama-Kishi conditions. Cinnoline-fused 10-membered ring enediyne is more reactive than corresponding carbocyclic analog and produces good yield of the Bergman cyclization product upon mild heating. This enediyne induces single-strand dDNA scissions upon incubation at 40 °C.
authors: Department of Chemistry, University of Georgia, Athens, Georgia 30602, USA.
authors: Olga V
authors: OV
authors: Vinogradova
authors: Irina A
authors: IA
authors: Balova
authors: Vladimir V
authors: VV
authors: Popik
mesh_terms: D003500:Cyclization; D053281:Enediynes / Q000138:chemical synthesis* / Q000737:chemistry; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry*; D015394:Molecular Structure; D013696:Temperature
chemical_list: D053281:Enediynes; D006574:Heterocyclic Compounds, 2-Ring; C476282:cinnoline