ω-氨甲基长叶烯的合成、表征及其抑菌活性  

Synthesis,Characterization and Antimicrobial Activity ofω-Aminomethyl Longifolene

作　　者：卢平平 黄焰群 甘月红 黄兰杰 葛海 黄道战 LU Pingping;HUANG Yanqun;GAN Yuehong;HUANG Lanjie;GE Hai;HUANG Daozhan(School of Chemistry and Chemical Engineering,Guangxi Minzu University,Key Laboratory of Chemistry and Engineering of Forest Products,State Ethnic Affairs Commission,Nanning 530008,China;Guangxi Key Laboratory of Chemistry and Engineer-ing of Forest Products,Guangxi Collaborative Innovation Center for Chemistry and Engineering of Forest Products,Nanning 530008,China;School of Materials and Environment,Guangxi Minzu University,Nanning 530105,China)

机构地区：[1]广西民族大学化学化工学院,林产化学与工程国家民委重点实验室,广西南宁530008 [2]广西林产化学与工程重点实验室,广西林产化学与工程协同创新中心,广西南宁530008 [3]广西民族大学材料与环境学院,广西南宁530105

出　　处：《林产化学与工业》2023年第6期8-16,共9页Chemistry and Industry of Forest Products

基　　金：广西自然科学基金资助项目(2017GXNSFAA198027)。

摘　　要：采用Gabriel合成法,由ω-氯甲基长叶烯(3)经中间体N-取代邻苯二甲酰亚胺衍生物(4)合成了目标化合物ω-氨甲基长叶烯(5)。化合物4和5的结构经高分辨质谱(HRMS)、傅里叶红外光谱(FT-IR)、核磁共振氢谱(1 H NMR)、核磁共振碳谱(13 C NMR)和单晶X射线衍射(SC-XRD)进行表征确证,化合物5的绝对构型由合成的化合物4的晶体结构推断。在化合物4的水解反应中,采用添加氢氧化钠在无溶剂下加热回流肼解的方法,能提高化合物5的产率,简化分离提纯工艺。单因素试验结果表明:较佳的肼解反应工艺条件为n(水合肼)∶n(化合物4)=23∶1、10%氢氧化钠溶液5 g、反应温度120℃、反应时间6 h,此条件下化合物5的产率为94.1%,纯度为99.98%。体外抗菌活性测定结果表明:化合物5对4种细菌(金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌和肺炎克雷伯菌)和3种真菌(白色念珠菌、热带念珠菌和黑曲霉)的生长有明显的抑制作用,其最低抑制质量浓度(MIC)分别为1.95、1.95、7.81、3.91、3.91、1.95和15.63 mg/L。其中化合物5对白色念珠菌和热带念珠菌的抑制活性强于阳性对照酮康唑。The target compound ofω-aminomethyl longifolene(5)was synthesized fromω-chloromethyl longifolene(3)by Gabriel synthesis via intermediate N-substituted phthalimide derivative(4).The structures of compounds 4 and 5 were confirmed by high resolution mass spectrum(HRMS),Fourier transform infrared(FT-IR),1H nuclear magnetic resonance(1 H NMR),13 C nuclear magnetic resonance(13 C NMR)and single-crystal X-ray diffraction(SC-XRD).The absolute configuration of compound 5 was inferred from the crystal structure of the synthesized compound 4.In the hydrolysis reaction of compound 4,the yield of compound 5 could be improved and the separation and purification process could be simplified by adding sodium hydroxide and heating reflux hydrazinolysis conditions under solvent-free.The results of single-factor experiment showed that under the optimum hydrazine hydrolysis conditions of n(hydrazine hydrate)∶n(compound 4)=23∶1,5 g 10%sodium hydroxide solution,and 6 h reaction time at reaction temperature of 120℃,the yield and purity of compound 5 could be reached 94.1%and 99.98%,respectively.The results of antibacterial activity assay in vitro showed that compound 5 could significantly inhibit the growth of four bacteria(Staphylococcus aureus,Bacillus subtilis,Escherichia coli and Klebsiella pneumoniae)and three fungi(Candida albicans,Candida tropicalis and Aspergillus niger).The minimum inhibitory concentrations(MIC)were 1.95,1.95,7.81,3.91,3.91,1.95 and 15.63 mg/L,respectively.Among them,compound 5 showed stronger inhibitory activities against C.albicans and C.tropicalis than positive control ketoconazole.

关 键 词：ω-氨甲基长叶烯 Gabriel合成 NaOH协同肼解 结构表征 抑菌活性 

分 类 号：TQ35[化学工程]