Department of Pharmaceutical Chemistry, Faculty of Pharmaceutical Sciences, Huachiew Chalermprakiet University, Samut Prakan 10540, Thailand.
Faculty of Pharmacy, Thammasat University, Pathumthani 12120, Thailand.
Molecules. 2023 Mar 31;28(7):3129. doi: 10.3390/molecules28073129.
Chromones are the structural building blocks of several natural flavonoids. The synthesis of chromones, which contain a hydroxy group on the ring, presents some challenges. We used the one-pot method to synthesize ten chromone derivatives and two related compounds using modified Baker-Venkataraman reactions. The structures were confirmed using FT-IR, H NMR, C NMR, and HRMS. The in vitro antioxidant assay revealed that compounds , , , and had potent antioxidant activity and that all these synthesized compounds, except those containing nitro groups, were harmless to normal cells. In addition, compounds , , , , , , and had anticancer activity. Compounds and were used to investigate the mechanism of anticancer activity. Both and induced a slightly early apoptotic effect but significantly impacted the S phase in the cell cycle. The effect on cell invasion indicates that both compounds significantly inhibited the growth of cervical cancer cells. A chromone scaffold possesses effective chemoprotective and antioxidant properties, making it a promising candidate for antioxidant and future cancer treatments.
色酮是几种天然类黄酮的结构构建块。含有羟基的色酮的合成具有一定的挑战性。我们使用一锅法,通过改良的 Baker-Venkataraman 反应,合成了十个色酮衍生物和两个相关化合物。通过傅里叶变换红外光谱(FT-IR)、氢核磁共振谱(H NMR)、碳核磁共振谱(C NMR)和高分辨率质谱(HRMS)确认了它们的结构。体外抗氧化测定表明,化合物 、 、 、 具有很强的抗氧化活性,除含有硝基的化合物外,所有合成的化合物对正常细胞均无害。此外,化合物 、 、 、 、 、 和 具有抗癌活性。化合物 和 被用于研究抗癌活性的机制。 和 都诱导了轻微的早期凋亡作用,但对细胞周期的 S 期有显著影响。对细胞侵袭的影响表明,两种化合物均能显著抑制宫颈癌的生长。色酮骨架具有有效的化学保护和抗氧化特性,使其成为抗氧化和未来癌症治疗的有前途的候选物。