On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous
(2022) Journal of Chemistry — Vol. 2022, p. 1-8 (2022)
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Valderrama, Jaime A. 
- Abstract
- Oximes are known for their anti-inflammatory, antimicrobial, antioxidant, and anticancer activities. Frequently, modification of biologically active carbonyl compounds into oximes leads to increased activity. The present study reports the reactivity of 2-alkanoylnaphthohydroquinones against hydroxylamine under aerial conditions. Results show that, depending on the structure of the hydroquinones, the reaction proceeds through two different chemical pathways to produce 2-(hydroxyamino)-1,4-naphthoquinone and their C-3 (hydroxyimino)alkyl derivatives. Both the formation of the quinoid compounds under aerial oxidation and C-C cleavage reactions of hemiaminal intermediates are discussed. In vitro screening of the substituted 1,4-naphthoquinones on a panel of cancer cells reveals moderate cytotoxic activities. Compound 19, 2-(hydroxyamino)-1,4-naphthoquinone, stands out by its anticancer potency against prostate cancer cells as shown by the lowest IC50 value (8.08 μM) and the best selectivity index (3.90). © 2022 Jaime A. Valderrama et al.
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Valderrama, J. A., Pérez-Herrera, A., Muccioli, G., Venegas-Casanova, E. A., Jara-Aguilar, R., Calderon, P. B., Benites, J., & Mitu, L. (2022). On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous. Journal of Chemistry, 2022, 1-8. https://doi.org/10.1155/2022/7664037 (Original work published 2022)