有机化学 ›› 2006, Vol. 26 ›› Issue (12): 1704-1708. 上一篇    下一篇

研究简报

-[2-(2-氨噻唑-4-基)-(Z)-2-甲氧亚胺乙酰胺基]-3-杂环硫亚甲基头孢菌素衍生物的半合成及抗菌活性

惠新平*,a,王勤b,王芳b,张自义*,a,管作武c   

  1. (a兰州大学化学化工学院 功能有机分子化学国家重点实验室 兰州 730000)
    (b兰州大学生命科学学院 兰州 730000)
    (c北京大学医学部 北京 100083)
  • 收稿日期:2006-01-13 修回日期:2006-03-13 发布日期:2006-11-21
  • 通讯作者: 张自义

Semisynthesis and Antibacterial Activity of 7β-[2-(2-Aminothiazol-4- yl)-(Z)-2-methoxyiminoacetylamido]-3-heterothiomethyl-cephalosporins

HUI Xin-Ping*,a,WANG Qinb,WANG Fangb,ZHANG Zi-Yi*,a,GUAN Zuo-Wuc   

  1. (a State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering,
    Lanzhou University
    , Lanzhou 730000)
    (b School of Life Sci-ences, Lanzhou University, Lanzhou 730000)
    (c Peking University Health Science Center, Beijing 100083)
  • Received:2006-01-13 Revised:2006-03-13 Published:2006-11-21
  • Contact: ZHANG Zi-Yi

通过5-取代-1,3,4-噁二唑-2-硫醇(2a2h), 5-芳胺基-1,3,4-噻二唑-2-硫醇(2i2j)和头孢菌素母体7-氨基头孢烷酸(7-ACA)反应, 制得头孢菌素中间体3a3j, 用氨噻唑肟活性酯4和头孢菌素中间体缩合, 合成了头孢菌素衍生物5a5j. 体外抗菌结果表明头孢菌素衍生物对革兰氏阳性菌和阴性菌均有显著抑制活性, 对金黄色葡萄球菌尤为敏感

关键词: 抗菌活性, 离心薄层层析, 头孢菌素, 半合成

New cephalosporin derivatives 5a5j were prepared by condensation of 3a~3j with aminothiazoleoxime active ester 4. The intermediates 3a3j were synthesized by the reaction of 5-substituted-1,3,4- oxadiazole-2-thiols (2a2h), 5-arylamino-1,3,4-thiadiazole-2-thiols (2i2j) with 7-aminocephalosporanic acid (7-ACA), respectively. The preliminary results of antibacterial activities revealed that compounds 5 showed obviously antibacterial activities against both Gram-positive and Gram-negative bacteria.

Key words: centrifugal-TLC, semisynthesis, antibacterial activity, cephalosporin