林产化学与工业2023，Vol.43Issue(6)：8-16,9.DOI:10.3969/j.issn.0253-2417.2023.06.002
ω-氨甲基长叶烯的合成、表征及其抑菌活性
Synthesis,Characterization and Antimicrobial Activity of ω-Aminomethyl Longifolene
摘要
Abstract
The target compound of ω-aminomethyl longifolene(5)was synthesized from ω-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),1 H 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Key words
ω-aminomethyl longifolene/Gabriel synthesis/NaOH collaborative hydrazine hydrolysis/structurally characterization/antimicrobial activity分类
化学化工引用本文复制引用
卢平平,黄焰群,甘月红,黄兰杰,葛海,黄道战..ω-氨甲基长叶烯的合成、表征及其抑菌活性[J].林产化学与工业,2023,43(6):8-16,9.基金项目
广西自然科学基金资助项目(2017GXNSFAA198027) （2017GXNSFAA198027）
