高等学校化学学报

高等学校化学学报 ›› 1999, Vol. 20 ›› Issue (10): 1564.

• 论文 • 上一篇    下一篇

3-杂环硫亚甲基头孢菌素衍生物的半合成及抗菌活性研究

郝兰1, 惠新平1, 张自义1, 管作武2, 何玉林3, 于红娟3   

  1. 1. 兰州大学化学化工学院, 兰州 730000;
    2. 北京医科大学应用药物研究所, 北京 100083;
    3. 兰州医学院微生物研究室, 兰州
  • 收稿日期:1999-01-28 出版日期:1999-10-24 发布日期:1999-10-24
  • 通讯作者: 张自义
  • 作者简介:郝兰,女,34岁,硕士,讲师,现在兰州医学院工作.

Studies on Semisynthesis and Antibacterial Activity of 3-Heterocyclicthiomethyl Cephalosporins

HAO Lan1, HUI Xin-Ping1, ZHANG Zi-Yi1, GUAN Zuo-Wu2, HE Yu-Lin3, YU Hong-Juan3   

  1. 1. National Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China;
    2. Institute of Applied Pharmacy, Beijing Medical University, Beijing 100083, China;
    3. Department of Microbiology, Lanzhou Medical College, Lanzhou 730000, China
  • Received:1999-01-28 Online:1999-10-24 Published:1999-10-24

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摘要： 通过取代噁二唑硫酮、噻二唑硫酮及三唑硫酮分别和头孢菌素母体7-ACA反应,制得14种7-氨基-3-杂环硫亚甲基头孢菌素新母体2a-2n,用1-芳基-5-甲基-1H-1,2,3-三唑-4-甲酰氯与头孢菌素新母体缩合,制得2种新的7β-(1-芳基-5-甲基-1H-1,2,3-三唑-4-甲酰胺基)-3-(2-取代1,3,4-bI二唑-5-硫亚甲基)头孢菌素4c,4d.新化合物结构经元素分析、IR、1HNMR及FAB-MS确认.初步体外抗菌结果表明,新母体化合物2对革兰氏阳性菌有抑制活性且在相同浓度下比7-ACA强20倍,而头孢菌素4c,4d对革兰氏阳性和阴性菌都有显著抑制活性.

关键词: 头孢菌素, 杂环, 半合成, 抗菌活性

Abstract: Fourteen new mother nucleus of 7-amino-3-heterocyclicthiomethyl cephalosporins 2a_2n were synthesized by the reaction of 7-ACA with 2-substituted 1,3,4-oxadiazol-5-thione-1a_1g, 2-arylamino-1,3,4-thiadiazol-5-thione 1h_1l or 1, 2, 4-triazoline-5-hione 1m, 1n. Two new compounds, 7-(1-aryl-5-methyl-1H-1,2,3-triazol-4-formylamido)-3-(2-substituted-1,3,4-oxadiazol-5-thiomethyl) cephalosporins 4c, 4d, were obtained by the acylation of 7-amino group of 2c, 2d with 1-aryl-5-methyl-1H-1,2,3-triazol-4-formyl chloride 3a, 3b. The structures of the compounds synthesized were confirmed by elementary analyses, IR, 1HNMR and FAB-MS. In preliminary antibacterial sensitivity test, the compounds 2a_2l were found to show higher antibacterial activity than 7-ACA against Gram-positive bacteria, 4c, 4d were found to have significant antibacterial activity against both Gram-positive and Gram-negative bacteria.

Key words: Cephalosporin, Heterocycle, Semisynthesis, Antibacterial activities

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