α -桐酸酰胺类化合物的合成及抑菌、抗癌活性研究

Synthesis,Antibacterial and Anticancer Activity ofα-Eleostearic Amides Derivatives

为了寻求具有潜在生物活性的α-桐酸酰胺衍生物,以α-桐酸为原料,制备得到了一系列α-桐酸酰胺衍生物:α-桐酸-3-甲基苯酰胺(3a)、α-桐酸-4-甲氧基苯酰胺(3b)、α-桐酸-4-三氟甲氧基苯酰胺(3c)、α-桐酸-4-氟苯酰胺(3d)、α-桐酸-3-氯苯酰胺(3e)、α-桐酸-2,3-二氯苯酰胺(3f)、α-桐酸-2-甲基环己酰胺(3g),并用FT-IR、^(1)H NMR、^(13)C NMR和HPLC-MS对产物进行了确证。生物活性实验结果表明:化合物3c对肝癌细胞HepG2、直肠癌细胞DLD-1和乳腺癌细胞MCF-7均有较好的抑制效果,其对肝癌细胞HepG2的半数抑制浓度(IC 50,55.58μmol/L)和5-氟尿嘧啶相近。所有目标化合物对大肠杆菌和金黄色葡萄球菌均具有一定的抑制活性,其中,化合物3f对金黄色葡萄球菌有良好的抑菌活性,IC 50为0.022μmol/L,与氨苄青霉素钠的抗菌效果相近,具有成为动物饲料中抗生素替代品的潜力。

In order to findα-eleostearic acid derivatives with potential biological activity,a series ofα-eleostearic amides derived fromα-eleostearic acid was synthesized:α-eleostearic-3-methylbenz-amide(3a),α-eleostearic-4-methoxybenz-amide(3b),α-eleostearic-4-trifluoromethbenz-amide(3c),α-eleostearic-4-fluorobenz-amide(3d),α-eleostearic-3-chlorobenz-amide(3e),α-eleostearic-2,3-dichlorobenz-amide(3f),α-eleostearic-3-methylcyclohexan-amide(3g).The products were confirmed by FT-IR,^(1)H NMR,^(13)C NMR and HPLC-MS.The results of biological activity experiments showed that compound 3c had good inhibitory effect on hepatocarcinoma cells HepG2,rectal carcinoma cells DLD-1 and breast cancer cells MCF-7.The 50%inhibition concentration of compound 3f on HepG2 was 55.58μmol/L,which was similar to the 50%inhibition concentration of 5-fluorouracil.All compounds had inhibitory activity against Staphyloccocus aureus and Escherichia coli.Moreover,compound 3f had preferable antibacterial activity against Staphyloccocus aureus,the 50%inhibition concentration was 0.022μmol/L,which was similar to ampicillin sodium and had the potential to replace antibiotics in animal feed.