Atropisomeric 1-phenylbenzimidazoles affecting microtubule organization: influence of axial chirality
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389030%3A_____%2F24%3A00602474" target="_blank" >RIV/61389030:_____/24:00602474 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15310/24:73626671
Result on the web
<a href="https://doi.org/10.1039/d4ob00863d" target="_blank" >https://doi.org/10.1039/d4ob00863d</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d4ob00863d" target="_blank" >10.1039/d4ob00863d</a>
Alternative languages
Result language
angličtina
Original language name
Atropisomeric 1-phenylbenzimidazoles affecting microtubule organization: influence of axial chirality
Original language description
Benzimidazoles are frequently used in medicinal chemistry. Their anticancer effect is among the most prominent biological activities exhibited by this scaffold. Although numerous benzimidazole derivatives have been synthesized, possible atropisomerism of ortho-substituted 1-phenylbenzimidazoles has been largely overlooked. The aim of this research was to synthesize a small library of novel atropisomeric benzimidazole derivatives and explore their biological activity in various cancer and normal human cell lines. The new unique structural motif provides an interesting 3D architecture with axial chirality, which further contributes to molecular complexity and specificity. Racemates and their separated atropisomers arrested the cell cycle, caused apoptosis, and affected microtubule organization in cancer cells in vitro at different intensities. Moreover, this phenomenon was also verified by the inhibition of endothelial cell migration. These results showed that (+)-atropisomers, especially 5n, exhibit a stronger effect and show promise as agents for cancer therapy.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic & Biomolecular Chemistry
ISSN
1477-0520
e-ISSN
1477-0539
Volume of the periodical
22
Issue of the periodical within the volume
34
Country of publishing house
GB - UNITED KINGDOM
Number of pages
15
Pages from-to
6966-6980
UT code for WoS article
001265780200001
EID of the result in the Scopus database
2-s2.0-85198663786