Wyszukiwarka
Indole-Acrylonitrile Derivatives as Potential Antitumor and Antimicrobial Agents—Synthesis, In Vitro and In Silico Studies
Abstrakt
A series of 2-(1H-indol-2-yl)-3-acrylonitrile derivatives, 2a–x, 3, 4a–b, 5a–d, 6a–b, and 7, were synthesized as potential antitumor and antimicrobial agents. The structures of the prepared compounds were evaluated based on elemental analysis, IR, 1H- and 13NMR, as well as MS spectra. X-ray crystal analysis of the representative 2-(1H-indol-2-yl)-3-acrylonitrile 2l showed that the acrylonitrile double bond was Z-configured. All compounds were screened at the National Cancer Institute (USA) for their activities against a panel of approximately 60 human tumor cell lines and the relationship between structure and in vitro antitumor activity is discussed. Compounds of interest 2l and 5a–d showed significant growth inhibition potency against various tumor cell lines with the mean midpoint GI50 values of all tests in the range of 0.38-7.91 mM. The prominent compound with remarkable activity (GI50 = 0.0244-5.06 mM) and high potency (TGI = 0.0866-0.938 mM) against some cell lines of leukemia (HL-60(TB)), non-small cell lung cancer (NCI-H522), colon cancer (COLO 205), CNS cancer (SF-539, SNB-75), ovarian cancer ((OVCAR-3), renal cancer (A498, RXF 393), and breast cancer (MDA-MB-468) was 3-[4-(dimethylamino)phenyl]-2-(1-methyl-1H-indol-2-yl)acrylonitrile (5c). Moreover, the selected 2-(1H-indol-2-yl)-3-acrylonitriles 2a–c and 2e–x were evaluated for their antibacterial and antifungal activities against Gram-positive and Gram-negative pathogens as well as Candida albicans. Among them, 2-(1H-indol-2-yl)-3-(1H-pyrrol-2-yl)acrylonitrile (2x) showed the most potent antimicrobial activity and therefore it can be considered as a lead structure for further development of antimicrobial agents. Finally, molecular docking studies as well as drug-likeness and ADME profile prediction were carried out.
Cytowania
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8
CrossRef
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0
Web of Science
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7
Scopus
Autorzy (9)
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Anita Kornicka
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Karol Gzella
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Katarzyna Garbacz Dr hab.
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Małgorzata Jarosiewicz
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Maria Gdaniec
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Joanna Fedorowicz
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Lukasz Balewski
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Jakub Kokoszka
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Pełna treść
- Wersja publikacji
- Accepted albo Published Version
- DOI:
- Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.3390/ph16070918
- Licencja
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Informacje szczegółowe
- Kategoria:
- Publikacja w czasopiśmie
- Typ:
- artykuły w czasopismach
- Opublikowano w:
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Pharmaceuticals
nr 16,
ISSN: 1424-8247 - Język:
- angielski
- Rok wydania:
- 2023
- Opis bibliograficzny:
- Kornicka A., Gzella K., Garbacz K., Jarosiewicz M., Gdaniec M., Fedorowicz J., Balewski L., Kokoszka J., Ordyszewska A.: Indole-Acrylonitrile Derivatives as Potential Antitumor and Antimicrobial Agents—Synthesis, In Vitro and In Silico Studies// Pharmaceuticals -Vol. 16,iss. 7 (2023), s.918-
- DOI:
- Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.3390/ph16070918
- Źródła finansowania:
-
- Publikacja bezkosztowa
- Weryfikacja:
- Politechnika Gdańska
wyświetlono 115 razy
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