N-(α-桐酸酰基)三唑类化合物的制备及其生物活性  

Synthesis and Biological Activity of N-(α-Eleostearic Acyl)Triazole Derivatives

作　　者：成江 谢普军[1,2] 黄立新 张彩虹[1,2] 刘璐婕 CHENG Jiang;XIE Pujun;HUANG Lixin;ZHANG Caihong;LIU Lujie(Institute of Chemical Industry of Forest Products,CAF,National Engineering Lab. for Biomass Chemical Utilization,Key Lab. of Chemical Engineering of Forest Products,National Forestry and Grassland Administration,Key Lab. of Biomass Energy and Material,Jiangsu Province,Nanjing 210042,China;Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources,Nanjing Forestry University,Nanjing 210037,China)

机构地区：[1]中国林业科学研究院林产化学工业研究所,生物质化学利用国家工程实验室,国家林业和草原局林产化学工程重点实验室,江苏省生物质能源与材料重点实验室,江苏南京210042 [2]南京林业大学江苏省林业资源高效加工利用协同创新中心,江苏南京210037

出　　处：《林产化学与工业》2022年第3期27-33,共7页Chemistry and Industry of Forest Products

基　　金：江苏省自然科学基金资助项目(BK20181124);国家重点研发计划资助项目(2017YFD0601001)。

摘　　要：以α-桐酸为原料,制备得到一系列N-(α-桐酸酰基)三唑类化合物:N-(α-桐酸酰基)-3,5-二溴-1,2,4-三唑(3a)、N-(α-桐酸酰基)-1,2,4-三唑(3b)、N-(α-桐酸酰基)-3-巯基-1,2,4-三唑(3c)、N-(α-桐酸酰基)-5-硝基-1,2,4-三唑(3d)、N-(α-桐酸酰基)-1,2,3苯骈三唑(3e)、3-α-桐酸酰基-1,2,4-三唑(3f)、4-α-桐酸酰基-1,2,4-三唑(3g),并用FT-IR、^(1)H NMR、^(13)C NMR和MS对产物进行了确证。生物活性实验结果表明:化合物3a和3e对肝癌细胞Hep G2、直肠癌细胞DLD-1和乳腺癌细胞MCF-7均有抑制效果,化合物3d对乳腺癌细胞MCF-7的半数抑制浓度(IC^(50),25.12μmol/L)优于阳性对照5-氟尿嘧啶(5-Fu)的抗肿瘤效果。所有目标化合物对白色念珠菌均具有较好的抑制活性,但对大肠杆菌和金黄色葡萄球菌的抑制效果不显著。化合物3e对白色念珠菌的IC^(50)达到22.69 mg/L,与阳性对照5-氟胞嘧啶的抗菌效果相近,具有作为药物开发的潜力。A series of N-(α-eleostearic acyl)triazole compounds derived fromα-eleostearic acid were synthesized:N-(α-eleostearic acyl)-3,5-dibromo-1,2,4-triazole(3a),N-(α-eleostearic acyl)-1,2,4-triazole(3b),N-(α-eleostearic acyl)-3-sulfhydryl-1,2,4-triazole(3c),N-(α-eleostearic acyl)-5-nitro-1,2,4-triazole(3d),N-(α-eleostearic acyl)-1,2,3-benzotriazole(3e),3-(α-eleostearic acyl)-1,2,4-triazole(3f),4-(α-eleostearic acyl)-1,2,4-triazole(3g).The products were confirmed by FT-IR,^(1)H NMR,^(13)C NMR and MS.The results of biological activity experiments showed that compound 3a and 3e had inhibitory effect on hepatocarcinoma cells Hep G2,rectal carcinoma cells DLD-1 and breast cancer cells MCF-7.The 50%inhibition concentration(IC^(50))of compound 3d on MCF-7 was 25.12μmol/L,which was better than the IC^(50) of 5-fluorouracil(5-Fu).All compounds had good inhibitory activity against Candida albicans,and inhibitory activities on against Escherichia coli and Staphylococcus aureus were not significant.The IC^(50) of compound 3e against Candida albicans was 22.96 mg/L,which was similar to 5-flucytosine and indicated that it had the potential of drug development.

关 键 词：α-桐酸 三唑 生物活性 衍生物 

分 类 号：TQ35[化学工程]