10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization: Synthesis and DNA Cleavage Ability

Natalia A. Danilkina, Andrey M. Rumyantsev, Anna L. Lyapunova, Alexander S. D'Yachenko, Alexander F. Khlebnikov, Irina A. Balova

Результат исследований: Научные публикации в периодических изданияхстатья

Аннотация

The Nicholas-type macrocyclization through NH-tosyl functional group has been found to be an efficient technique for the synthesis of a 10-membered azaenediyne system annulated with a benzothiophene. To compare the activity of azaenediyne synthesized with similar oxa- and carbocyclic enediynes the Bergman cyclization activation energies and the ability of enediynes to cleave DNA (pBR322 plasmid) were investigated. The order of reactivity predicted by DFT calculations (N -enediyne < C -enediyne < O -enediyne) was confirmed by DSC analysis data. Surprisingly azaenediyne was found to be more active in the DNA cleavage assay than the C-analogue.

Язык оригиналаанглийский
Страницы (с-по)161-166
ЖурналSynlett
Том30
Номер выпуска2
DOI
СостояниеОпубликовано - 1 янв 2019

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