10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization: Synthesis and DNA Cleavage Ability
1
Institute of Chemistry
2
Department of Genetics and Biotechnology
Publication type: Journal Article
Publication date: 2018-12-11
scimago Q3
wos Q3
SJR: 0.437
CiteScore: 3.3
Impact factor: 1.4
ISSN: 09365214, 14372096
Organic Chemistry
Abstract
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.
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15
Total citations:
15
Citations from 2024:
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(46.67%)
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GOST
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Balova I. A. et al. 10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization: Synthesis and DNA Cleavage Ability // Synlett. 2018. Vol. 30. No. 02. pp. 161-166.
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Balova I. A., Danilkina N., Rumyantsev A., Lyapunova A., Dyachenko A., Khlebnikov A. F. 10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization: Synthesis and DNA Cleavage Ability // Synlett. 2018. Vol. 30. No. 02. pp. 161-166.
Cite this
RIS
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TY - JOUR
DO - 10.1055/s-0037-1610352
UR - https://doi.org/10.1055/s-0037-1610352
TI - 10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization: Synthesis and DNA Cleavage Ability
T2 - Synlett
AU - Balova, Irina A.
AU - Danilkina, Natalia
AU - Rumyantsev, Andrey
AU - Lyapunova, Anna
AU - Dyachenko, Alexander
AU - Khlebnikov, Alexander F
PY - 2018
DA - 2018/12/11
PB - Georg Thieme Verlag KG
SP - 161-166
IS - 02
VL - 30
SN - 0936-5214
SN - 1437-2096
ER -
Cite this
BibTex (up to 50 authors)
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@article{2018_Balova,
author = {Irina A. Balova and Natalia Danilkina and Andrey Rumyantsev and Anna Lyapunova and Alexander Dyachenko and Alexander F Khlebnikov},
title = {10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization: Synthesis and DNA Cleavage Ability},
journal = {Synlett},
year = {2018},
volume = {30},
publisher = {Georg Thieme Verlag KG},
month = {dec},
url = {https://doi.org/10.1055/s-0037-1610352},
number = {02},
pages = {161--166},
doi = {10.1055/s-0037-1610352}
}
Cite this
MLA
Copy
Balova, Irina A., et al. “10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization: Synthesis and DNA Cleavage Ability.” Synlett, vol. 30, no. 02, Dec. 2018, pp. 161-166. https://doi.org/10.1055/s-0037-1610352.