Wyszukiwarka
Synthesis and Structure of Novel Hybrid Compounds Containing Phthalazin-1(2H)-imine and 4,5-Dihydro-1H-imidazole Cores and Their Sulfonyl Derivatives with Potential Biological Activities
Abstrakt
A novel hybrid compound—2-(4,5-dihydro-1H-imidazol-2-yl)phthalazin-1(2H)-imine (5) was synthesized and converted into di-substituted sulfonamide derivatives 6a–o and phthalazine ring opening products—hydrazonomethylbenzonitriles 7a–m. The newly prepared compounds were characterized using elemental analyses, IR and NMR spectroscopy, as well as mass spectrometry. Single crystal X-ray diffraction data were collected for the representative compounds 5, 6c, 6e, 7g, and 7k. The antiproliferative activity of compound 5, sulfonyl derivatives 6a–o and benzonitriles 7a–m was evaluated on approximately sixty cell lines within nine tumor-type subpanels, including leukemia, lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast. None of the tested compounds showed any activity against the cancer cell lines used. The antioxidant properties of all compounds were assessed using the DPPH, ABTS, and FRAP radical scavenging methods, as well as the β-carotene bleaching test. Antiradical tests revealed that among the investigated compounds, a moderate ABTS antiradical effect was observed for sulfonamide 6j (IC50 = 52.77 µg/mL). Benzonitrile 7i bearing two chlorine atoms on a phenyl ring system showed activity in a β-carotene bleaching test (IC50 = 86.21 µg/mL). Finally, the interaction AGE/RAGE in the presence of the selected phthalazinimines 6a, 6b, 6g, 6m, and hydrazonomethylbenzonitriles 7a, 7c–g, and 7i–k was determined by ELISA assay. A moderate inhibitory potency toward RAGE was found for hydrazonomethylbenzonitriles—7d with an electron-donating methoxy group (R = 3-CH3O-C6H4) and 7f, 7k with an electron-withdrawing substituent (7f, R = 2-Cl-C6H4; 7k, R = 4-NO2-C6H4).
Cytowania
-
0
CrossRef
-
0
Web of Science
-
0
Scopus
Autorzy (8)
-
Łukasz Balewski dr. inż.
-
Maria Gdaniec
-
Anna Herring dr
-
Christophe Furman
-
Alina Ghinet
-
Jakub Kokoszka
-
Anita Kornicka
Cytuj jako
Pełna treść
pełna treść publikacji nie jest dostępna w portalu
Słowa kluczowe
Informacje szczegółowe
- Kategoria:
- Publikacja w czasopiśmie
- Typ:
- artykuły w czasopismach
- Opublikowano w:
-
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
nr 25,
ISSN: 1661-6596 - Język:
- angielski
- Rok wydania:
- 2024
- Opis bibliograficzny:
- Balewski Ł., Gdaniec M., Herring A., Furman C., Ghinet A., Kokoszka J., Ordyszewska A., Kornicka A.: Synthesis and Structure of Novel Hybrid Compounds Containing Phthalazin-1(2H)-imine and 4,5-Dihydro-1H-imidazole Cores and Their Sulfonyl Derivatives with Potential Biological Activities// INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES -,iss. 25/21 (2024), s.11495-
- DOI:
- Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.3390/ijms252111495
- Źródła finansowania:
-
- IDUB
- Weryfikacja:
- Politechnika Gdańska
wyświetlono 4 razy
Publikacje, które mogą cię zainteresować
Novel 5-Substituted 2-(Aylmethylthio)-4-chloro-N-(5-aryl-1,2,4-triazin-3-yl)benzenesulfonamides: Synthesis, Molecular Structure, Anticancer Activity, Apoptosis-Inducing Activity and Metabolic Stability
- B. Żołnowska,
- J. Sławiński,
- A. Pogorzelska
- + 7 autorów
Synthesis of 3-(2-Alkylthio-4-chloro-5-methylbenzenesulfonyl)-2-(1-phenyl-3-arylprop-2-enylideneamino)guanidine Derivatives with Pro-Apoptotic Activity against Cancer Cells
- A. Pogorzelska,
- J. Sławiński,
- A. Kawiak
- + 2 autorów
Novel 2-(2-arylmethylthio-4-chloro-5-methylbenzenesulfonyl)-1-(1,3,5-triazin-2-ylamino)guanidine derivatives: Inhibition of human carbonic anhydrase cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII, anticancer activity, and molecular modeling studies
- B. Żołnowska,
- J. Sławiński,
- K. Szafrański
- + 7 autorów