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).

中文翻译：

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关于 2-烷酰基萘氢醌与羟胺的反应：获得细胞毒性 2-(羟基氨基)-1,4-萘醌及其 3-(羟基亚氨基)烷基类似物

肟以其抗炎、抗菌、抗氧化和抗癌活性而闻名。通常，将具有生物活性的羰基化合物修饰成肟会导致活性增加。本研究报告了 2-烷酰基萘氢醌在空气条件下对羟胺的反应性。结果表明，根据氢醌的结构，反应通过两种不同的化学途径进行，生成 2-(羟基氨基)-1,4-萘醌及其 C-3(羟基亚氨基)烷基衍生物。讨论了空气氧化下醌类化合物的形成和半胺中间体的 CC 裂解反应。在一组癌细胞上对取代的 1,4-萘醌进行体外筛选显示出中等的细胞毒活性。化合物19, 2-(hydroxyamino)-1,4-naphthoquinone 因其对前列腺癌细胞的抗癌效力而脱颖而出，如最低的 IC ₅₀值 (8.08  μM ) 和最佳的选择性指数 (3.90) 所示。