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2013 , Vol. 33 >Issue 10: 2196 - 2204

DOI: https://doi.org/10.6023/cjoc201305027

研究论文

新型蒎烷基含氮杂环化合物的合成及抑菌活性研究

  • 魏柏松 ,
  • 谷文 ,
  • 徐徐 ,
  • 杨益琴 ,
  • 王石发
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  • a 南京林业大学化学工程学院 南京 210037;
    b 江苏省生物质绿色燃料与化学品重点实验室 南京 210037;
    c 南京林业大学轻工科学与工程学院 南京 210037

收稿日期: 2013-05-15

  修回日期: 2013-06-06

  网络出版日期: 2013-06-21

基金资助

国家自然科学基金(No. 31170538)资助项目

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Synthesis and Antibacterial Activity of New Pinanyl Nitrogen-Containing Heterocycles

  • Wei Baisong ,
  • Gu Wen ,
  • Xu Xu ,
  • Yang Yiqin ,
  • Wang Shifa
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  • a College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037;
    b Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, Nanjing 210037;
    c College of Light Industry and Engineering, Nanjing Forestry University, Nanjing 210037

Received date: 2013-05-15

  Revised date: 2013-06-06

  Online published: 2013-06-21

Supported by

Project supported by the National Natural Science Foundation of China (No. 31170538).

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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.

关键词： (-)-α-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

本文引用格式

魏柏松 , 谷文 , 徐徐 , 杨益琴 , 王石发 . 新型蒎烷基含氮杂环化合物的合成及抑菌活性研究[J]. 有机化学, 2013 , 33(10) : 2196 -2204 . DOI: 10.6023/cjoc201305027

Abstract

New types of pinanyl-2-aminopyrimidines and pinanyl isoxazolines were synthesized from (-)-α-pinene. (-)-α-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 1H NMR, 13C 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. coli.

Key words： (-)-α-pinene; 4-arylidene-2-hydroxy-3-pinanones; pinanyl-2-aminopyrimidines; pinanyl isoxazolines; antibacterial activity

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