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

Aly, A. A.; Hassan, A. A.; Mohamed, N. K.; Ramadan, M.; Abd El-Aal, A. S.; Bräse, S.; Nieger, M.

Abstract:
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.

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Verlagsausgabe §
DOI: 10.5445/IR/1000127695
Veröffentlicht am 15.12.2020
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2020
Sprache Englisch
Identifikator ISSN: 0308-2342, 0308-2350, 1747-5198
KITopen-ID: 1000127695
HGF-Programm 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in Journal of chemical research
Verlag Science Reviews 2000
Vorab online veröffentlicht am 24.11.2020
Schlagwörter 1,2,4-triazolospiro[4,5]deca-2,6,9-trien-8-ones, 2-chloro-1,4-benzoquinone, 5-hydroxy-1,4-naphthoquinone, 5-hydroxy-2-(piperidin-1-yl)naphthalene-1,4-dione, amidrazones, benzo[e][1,2,4]triazines
Nachgewiesen in Scopus
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