School of Chemistry, Universidad Autónoma de San Luis Potosí, Av. Manuel Nava No. 6, SLP 78210, Mexico.
Laboratorio de microRNAs y Cáncer, Unidad Académica de Ciencias Biológicas, Universidad Autónoma de Zacatecas, Av. Preparatoria No.301, ZAC 98068, Mexico.
Molecules. 2019 Nov 25;24(23):4285. doi: 10.3390/molecules24234285.
We performed an extensive analysis about the reaction conditions of the 1,4-Michael addition of amino acids to 1,4-naphthoquinone and substitution to 2,3-dichloronaphthoquinone, and a complete evaluation of stoichiometry, use of different bases, and the pH influence was performed. We were able to show that microwave-assisted synthesis is the best method for the synthesis of naphthoquinone-amino acid and chloride-naphthoquinone-amino acid derivatives with 79-91% and 78-91% yields, respectively. The cyclic voltammetry profiles showed that both series of naphthoquinone-amino acid derivatives mainly display one quasi-reversible redox reaction process. Interestingly, it was shown that naphthoquinone derivatives possess a selective antitumorigenic activity against cervix cancer cell lines and chloride-naphthoquinone-amino acid derivatives against breast cancer cell lines. Furthermore, the newly synthetized compounds with asparagine-naphthoquinones ( and ) inhibited ~85% of SiHa cell proliferation. These results show promising compounds for specific cervical and breast cancer treatment.
我们对氨基酸与 1,4-萘醌的 1,4-Michael 加成反应条件以及取代 2,3-二氯萘醌的反应条件进行了广泛分析，并对反应的化学计量比、不同碱的使用以及 pH 值的影响进行了全面评估。我们能够证明，微波辅助合成是合成萘醌-氨基酸和氯代萘醌-氨基酸衍生物的最佳方法，产率分别为 79-91%和 78-91%。循环伏安曲线表明，这两个系列的萘醌-氨基酸衍生物主要显示一个准可逆的氧化还原反应过程。有趣的是，萘醌衍生物对宫颈癌细胞系具有选择性的抗肿瘤活性，而氯代萘醌-氨基酸衍生物对乳腺癌细胞系具有抗肿瘤活性。此外，新合成的含天冬酰胺-萘醌（和）化合物抑制了约 85%的 SiHa 细胞增殖。这些结果表明，这些化合物具有针对特定宫颈癌和乳腺癌的治疗潜力。
