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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
- 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).
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