A family of substituted hydrazonoisoxazolones with potential biological properties

Bustos C.; Molins E.; Cárcamo J.-G.; Aguilar M.N.; Sánchez C.; Moreno-Villoslada I.; Nishide H.; Zarate X.; Schott E.

dc.contributor.author	Bustos C.
dc.contributor.author	Molins E.
dc.contributor.author	Cárcamo J.-G.
dc.contributor.author	Aguilar M.N.
dc.contributor.author	Sánchez C.
dc.contributor.author	Moreno-Villoslada I.
dc.contributor.author	Nishide H.
dc.contributor.author	Zarate X.
dc.contributor.author	Schott E.
dc.date.accessioned	2020-09-02T22:13:37Z
dc.date.available	2020-09-02T22:13:37Z
dc.date.issued	2016
dc.identifier	10.1039/c5nj02604k
dc.identifier.citation	40, 3, 2156-2167
dc.identifier.issn	11440546
dc.identifier.uri	https://hdl.handle.net/20.500.12728/3816
dc.description	The synthesis, characterization and biological study of a new 3,4,5-trisubstituted isoxazolones have been reported, whereby a series of (Z)-3-methyl-4-(2-(R-phenyl)hydrazinylidene)isoxazol-5(4H)-ones were prepared by the reaction of a β-diketohydrazone with hydroxylammonium chloride. All the products were characterized using EA, UV-Vis, FT-IR, 1H-NMR, 13C-NMR spectroscopy and HMBC. The crystalline and molecular structures of three compounds were solved by X-ray diffraction methods. Density functional theory (DFT) and time-dependent DFT (TDDFT) calculations were performed to obtain a better explanation of the observed experimental behaviour of these newly synthetized compounds. Furthermore, the reports of cytotoxicity and an antiproliferative effect in human promyelocytic leukaemia cells, HL-60, was tested by the MTT reduction method, showing that most of the newly synthetized compounds had important antineoplastic activity. The most active isoxazolones were used in reverse transcription polymerase chain reaction (RT-PCR) experiments to determine the effect on the expression levels on mRNA encoding using the anti-apoptotic, Bcl 2, pro-apoptotic, Bax, and the proliferation inhibition, p21WAF-1, proteins. Therefore, it was possible to fully characterize the complete library of 15 isoxazolones and to show that most of them are antineoplastic trough an apoptotic pathway. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016.
dc.language.iso	en
dc.publisher	Royal Society of Chemistry
dc.title	A family of substituted hydrazonoisoxazolones with potential biological properties
dc.type	Article

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A family of substituted hydrazonoisoxazolones with potential biological properties

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