Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 16, Pages 6937-6941Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201148h
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Funding
- Georgia Cancer Coalition
- Saint-Petersburg State University [12.38.14.2011]
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A short and efficient synthesis of cinnoline-fused cyclic enediyne is reported. Richter cydization 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 degrees C.
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