Synthesis and Antitumor Activities of Quercetin-3-O-Ethylaniline Derivatives
SHAO Xiang-min1, CONG Yang1, MENG Fan-hua1, YAN Zi-tong2, ZHAI Guang-yu1*
1. School of Pharmacy and Chemical Engineering, Zhengzhou University of Industrial Technology, Zhengzhou 451100, China; 2. School of Pharmacy, Zhengzhou University, Zhengzhou 450001, China
Abstract：OBJECTIVE To synthesize quercetin-3-O-ethylaniline derivatives and test their antitumor activity. METHODS Quercetin was used as the leader to selectively modify the hydroxyl group at the 3-position of the C ring. Using rutin as raw material, after selective protection of benzyl group, Williamson ether formation reaction, and Pd/C catalyzed hydrogenation and debenzylation, 13 quercetin-3-O-ethylaniline derivatives were obtained, all of which have not been reported in the literature. The structures of the target products were confirmed by 1H-NMR, 13C-NMR, and ESI-MS. The MTT method was used to investigate the proliferation inhibitor effects of 13 quercetin-3-O-ethylaniline derivatives on human esophageal squamous cell carcinoma (EC109), human gastric cancer (HGC27), human breast cancer (MCF-7), and mouse melanoma (B16-F10). RESULTS After structural modification of quercetin by chemical methods, the anti-tumor activity in vitro is enhanced. Among them, the inhibitory effects of compound 5c(5.229±0.371) and 5e(2.628±0.087) on mouse melanoma (B16-F10) are better than 5-fluorouracil (5-FU) (14.376±0.272). CONCLUSION Compounds 5c and 5e are worthy of further study as low toxicity anti-melanoma candidates.
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2023, Vol. 58 
