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On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous

Authors :
Jaime A. Valderrama
Andrea Pérez-Herrera
Giulio G. Muccioli
Edmundo A. Venegas-Casanova
Rafael Jara-Aguilar
Pedro Buc Calderon
Julio Benites
Source :
Journal of Chemistry, Vol 2022 (2022)
Publication Year :
2022
Publisher :
Hindawi Limited, 2022.

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).

Subjects

Subjects :
Chemistry
QD1-999

Details

Language :
English
ISSN :
20909071
Volume :
2022
Database :
Directory of Open Access Journals
Journal :
Journal of Chemistry
Publication Type :
Academic Journal
Accession number :
edsdoj.896959ef273b400cb700e199f407e506
Document Type :
article
Full Text :
https://doi.org/10.1155/2022/7664037