Synthesis of quinone-based heterocycles of broad-spectrum anticancer activity

Autor: Mohamed Ramadan, Martin Nieger, Stefan Braese, Ashraf A. Aly, Amal S. Abd El-Aal, Nasr K. Mohamed, Alaa A. Hassan
Přispěvatelé: Department of Chemistry
Rok vydání: 2020
Předmět:
Zdroj: Journal of Chemical Research. 45:562-571
ISSN: 2047-6507
1747-5198
DOI: 10.1177/1747519820959737
Popis: A synthesis of benzo[ e][1,2,4]triazines and 1,2,4-triazolospiro[4,5]deca-2,6,9-trien-8-ones has been developed from reactions of amidrazones with 2-chloro-1,4-benzoquinone in EtOAc containing 0.5 mL of piperidine. This highly regioselective and one-pot process provided rapid access to 1,2,4-triazolospiro[4,5]deca-2,6,9-trien-8-ones (60%–70%) and benzo[ e][1,2,4]triazines (11%–18%). On reacting amidrazones with 5-hydroxy-1,4-naphthoquinone in an EtOAc/piperidine mixture, the reaction proceeded to give 5-hydroxy-2-(piperidin-1-yl)naphthalene-1,4-dione. The structures of the isolated products were proved by infrared, NMR (2D-NMR), mass spectra, and elemental analyses in addition to X-ray structure analysis. The reaction mechanisms are discussed. The anticancer screening of selected compounds showed broad-spectrum anticancer activity against most melanoma cancer cell lines, ovarian cancer OVCAR-3, central nervous system cancer SF-295 and U251, non-small cell lung cancer NCI-H23, renal cancer SN12C, and colon cancer HCT-15 and HCT-116. The selected compounds exhibited moderate to weak anticancer activity to other cell lines.
Databáze: OpenAIRE
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