Synthesis, Cytotoxic, and Antioxidant Activity of Some Benzoquinoline-Based Heterocycles

A series of benzoquinoline-based heterocycles was synthesized using 2-((3-chlorobenzo[f]quinolin-2-yl)methylene)hydrazine-1-carbothioamide as a key material via condensation of 3-chlorobenzo[f]quinoline-2-carbaldehyde with thiosemicarbazide. The titled thiosemicarbazone scaffold was conducted with s...

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Bibliographic Details
Published in:Polycyclic aromatic compounds 2024-10, Vol.44 (9), p.5938-5950
Main Authors: El-Helw, Eman A. E., Asran, Mahmoud, Azab, Mohammad E., Helal, Maher H., Ramadan, Sayed K.
Format: Article
Language:English
Subjects:
Acetanilide
Acetic anhydride
Antioxidant
Antioxidants
Antitumor
Antitumor agents
Benzoquinoline
Chloroacetic acid
Condensates
Cytotoxicity
Heterocyclic compounds
Hydrazine
Hydrazines
Quinoline
Reagents
Synthesis
Thiosemicarbazone
Triazole thione
Triazoles
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Summary:A series of benzoquinoline-based heterocycles was synthesized using 2-((3-chlorobenzo[f]quinolin-2-yl)methylene)hydrazine-1-carbothioamide as a key material via condensation of 3-chlorobenzo[f]quinoline-2-carbaldehyde with thiosemicarbazide. The titled thiosemicarbazone scaffold was conducted with some carbon electrophilic reagents such as acetic anhydride, chloroacetyl chloride, chloroacetic acid, 2-bromo-1-(3-nitrophenyl)ethan-1-one, 2-chloro-N-phenylacetamide, and dimethyl but-2-ynedioate to obtain triazole thione, imidazolone, thiazolidinone, and thiazole derivatives. On the other hand, hydrazinolysis of thiosemicarbazone did not proceed as expected but it gave the azine derivative. The in vitro antitumor and antioxidant activity of the synthesized compounds were screened and revealed that triazole thione and thiazole derivatives were the most potent.
ISSN:1040-6638
1563-5333
DOI:10.1080/10406638.2023.2270767