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

Выдержка

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
Номер статьиst-2018-b0536-l
Страницы (с-по)161-166
Число страниц6
ЖурналSynlett
Том30
Номер выпуска2
DOI
СостояниеОпубликовано - 1 янв 2019

Отпечаток

Enediynes
DNA
Cyclization
Discrete Fourier transforms
Functional groups
Assays
Plasmids
Activation energy
benzothiophene

Предметные области Scopus

  • Органическая химия

Цитировать

Danilkina, Natalia A. ; Rumyantsev, Andrey M. ; Lyapunova, Anna L. ; D'Yachenko, Alexander S. ; Khlebnikov, Alexander F. ; Balova, Irina A. / 10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization : Synthesis and DNA Cleavage Ability. В: Synlett. 2019 ; Том 30, № 2. стр. 161-166.
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10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization : Synthesis and DNA Cleavage Ability. / Danilkina, Natalia A.; Rumyantsev, Andrey M.; Lyapunova, Anna L.; D'Yachenko, Alexander S.; Khlebnikov, Alexander F.; Balova, Irina A.

В: Synlett, Том 30, № 2, st-2018-b0536-l, 01.01.2019, стр. 161-166.

Результат исследований: Научные публикации в периодических изданияхстатья

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T2 - Synthesis and DNA Cleavage Ability

AU - Danilkina, Natalia A.

AU - Rumyantsev, Andrey M.

AU - Lyapunova, Anna L.

AU - D'Yachenko, Alexander S.

AU - Khlebnikov, Alexander F.

AU - Balova, Irina A.

PY - 2019/1/1

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KW - Bergman cyclization

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KW - iodocyclization

KW - Nicholas reaction

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