文献类型：期刊文献

中文题名：异海松酸糠醛类酰腙化合物的合成及生物活性研究

英文题名：Synthesis and Biological Activity of Isopimaric Furfural Acylhydrazone Derivatives

作者：卢言菊[1,2,3] 赵振东[1,2,3] 王婧[1,2,3] 徐士超[1,2,3] 毕良武[1,2,3] 陈玉湘[1,2,3]

第一作者：卢言菊

机构：[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;[3]中国林业科学研究院林业新技术研究所,北京100091

年份：2019

卷号：39

期号：3

起止页码：43-48

中文期刊名：林产化学与工业

外文期刊名：Chemistry and Industry of Forest Products

收录：CSTPCD;;Scopus;北大核心:【北大核心2017】；CSCD:【CSCD2019_2020】；

基金：中国林科院中央级公益性科研院所基本科研业务费专项资金(CAFYBB2017QA018);国家自然科学基金资助项目(31370575)

语种：中文

中文关键词：异海松酸;糠醛;合成;表征;生物活性

外文关键词：isopimaric acid;furfural;synthesis;characterization;biological activity

分类号：TQ351

摘要：以异海松酸为原料,采用先酰氯化后与水合肼反应的方法,制备得到异海松酸酰肼,然后再与不同取代基的糠醛发生反应,制备得到5种异海松酸糠醛类酰腙化合物:异海松酸基(糠醛)酰腙(4a)、异海松酸基(5-甲基糠醛)酰腙(4b)、异海松酸基(5-羟甲基糠醛)酰腙(4c)、异海松酸基(5-溴-2-糠醛)酰腙(4d)和异海松酸基(5-(4-溴苯基)糠醛)酰腙(4e),并采用FT-IR、1 H NMR、13 C NMR和MS对产物结构进行了确证。生物活性测定结果表明:目标化合物对肺炎链球菌、肺炎克雷伯氏菌、大肠杆菌、表皮葡萄球菌和金黄色葡萄球菌这5种菌种均具有一定的抑制活性,其中4a对肺炎克雷伯氏菌具有很好的抑菌活性,最低抑菌浓度为1.95 mg/L,化合物4c对肺炎链球菌具有非常好的抑菌活性,最低抑菌浓度仅为0.98 mg/L。当异海松酸糠醛类酰腙化合物的浓度为100μmol/L时,化合物4d对人体肝癌(Hep G2)、乳腺癌(MDA-MB-231)、前列腺癌(PC-3)和宫颈癌(Hela)这4种人体肿瘤细胞均具有较高的抑制率,其抑制率分别为75.17%、82.33%、78.52%和80.97%;化合物4e对人体肝癌(Hep G2)的抑制率高达93.68%,说明其对人体肝癌细胞具有很强的抑制活性。
Hydrazine of isopimaric acid was synthesized by first chlorination then reaction with hydrazine hydrate using isopimaric acid as raw material.A series of novel isopimaric furfural acylhydrazone derivatives such as isopimaric acid 2-furaldehyde acylhydrazone(4a),isopimaric acid(5-methyl-2-furancarboxaldehyde)acylhydrazone(4b),isopimaric acid(5-hydroxymethylfurfural)acylhydrazone(4c),isopimaric acid(5-bromo-2-furaldehyde)acylhydrazone(4d)and isopimaric acid(5-hydroxymethylfurfural)acylhydrazone(4c),isopimaric acid(5-(4-bromopheny)furfural)acylhydrazone(4e)were synthesized by the condensation reactions of furfural with different substituent and intermediate hydrazine of isopimaric acid.The structures of isopimaric furfural acylhydrazone derivatives were characterized and indentified by FT-IR,1 H NMR,13 C NMR and MS.The results showed that most of the target compounds exhibited a certain fungicidal activity on Streptococcus pneumoniae,Klebsiella pneumoniae,Escherichia coli,Staphylococcus epidermidisand and S.aureus,in which the minimal inhibitory concentration(MIC)of 4a against Klebsiella pneumoniae is 1.95 mg/L;the minimal inhibitory concentration(MIC)of 4c against Streptococcus pneumoniae is 0.98 mg/L.Compound 4d had inhibition rate of 75.17%,82.33%,78.52%and 80.97%against hepatocarcinoma cells(Hep G2),breast cancer cells(MDA-MB-231),prostate cancer(PC-3),and cervical cancer(Hela)at the concentration of 100μmol/L;Compound 4e had inhibition rate of 93.68%against Hep G2 at the concentration of 100μmol/L,indicating that compound 4e had a strong inhibitory activity on human hepatoma cells.