On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous
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 hydroxyl...
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| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Wiley
2022-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2022/7664037 |
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| Summary: | 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). |
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| ISSN: | 2090-9071 |