新型蒎烷基含氮杂环化合物的合成及抑菌活性研究  

Synthesis and Antibacterial Activity of New Pinanyl Nitrogen-Containing Heterocycles

作　　者：魏柏松[1] 谷文[1,2] 徐徐[1,2] 杨益琴[3] 王石发[1,2] 

机构地区：[1]南京林业大学化学工程学院,南京210037 [2]江苏省生物质绿色燃料与化学品重点实验室,南京210037 [3]南京林业大学轻工科学与工程学院,南京210037

出　　处：《有机化学》2013年第10期2196-2204,共9页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.31170538)资助项目~~

摘　　要：以(-)-α-蒎烯为原料,合成了新型蒎烷基-2-氨基嘧啶类化合物和蒎烷基异噁唑啉类化合物.(-)-α-蒎烯经选择性氧化得到(+)-2-羟基-3-蒎酮;(+)-2-羟基-3-蒎酮与多种芳香醛缩合制得4-芳亚甲基-2-羟基-3-蒎酮类化合物2a^2f;在NaOH溶液或叔丁醇钾中,再与盐酸胍或盐酸羟胺反应,合成了蒎烷基-2-氨基嘧啶类化合物3a^3e和异噁唑啉类化合物4a^4d.采用1H NMR,13C NMR,FT-IR,GC-MS和元素分析等手段对所合成化合物的结构进行表征.考察了化合物3a^3e和4a^4d对白色念珠菌(C.albicans)、黑曲霉(A.niger)、热带假丝酵母(G.tropicalis)、大肠杆菌(E.coli)、金黄色葡萄球菌(S.aureus)、枯草芽孢杆菌(B.subtilis)、荧光假单胞菌(P.fluorescens)等的抑制活性.结果表明,化合物3b,3e对大肠杆菌和枯草芽孢杆菌有很强的抑制作用;化合物3a,3d,4b和4d对大肠杆菌表现出较强的抑制活性.New types of pinanyl-2-aminopyrimidines and pinanyl isoxazolines were synthesized from （--）-a-pinene. （--）-a-Pinene was selectively oxidized into （＋）-2-hydroxy-3-pinanone, which was condensed with aromatic aldehydes to obtain 4-arylidene-2-hydroxy-3-pinanones 2a^2f. Pinanyl-2-aminopyrimidines 3a^3e and pinanyl isoxazolines 4a^4d were prepared by cyclization of 4-arylidene-2-hydroxy-3-pinanones with guanidine hydrochloride and hydroxylamine hydrochloride under catalysis of NaOH or t-BuOK. The structures of the synthesized compounds were determined by IH NMR, ~3C NMR, FT-IR, GC-MS, and elemental analyses. Antibacterial and antifungal activities tests of the synthesized pinanyl-2-aminopyri- midines 3a^3e and pinanyl isoxazolines 4a^4d against C. albicans, A. niger, G. tropicalis, E. coli, S. aureus, B. subtilis, and P. fluorescens were also carried out, and it has been observed that compounds 3b and 3e had strong antibacterial effects to E. coli and B. subtilis, 3a, 3d, 4b and 4d had good activities to E. coll.

关 键 词：(-)-d-蒎烯 4-芳亚甲基-2-羟基-3-蒎酮 蒎烷基-2-氨基嘧啶 蒎烷基异噁唑啉 抑菌活性 

分 类 号：O621.3[理学—有机化学] R284[理学—化学]