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有机化学 ›› 2007, Vol. 27 ›› Issue (05): 607-618. 上一篇    下一篇

研究论文

3-杂环基硫取代-1,3,4,5-四氢-2-氧代-苯并氮杂衍生物的合成

邱早早a，张欢欢a，惠新平a，许鹏飞*,a
王勤b，杜宇平b，杨洋b   

  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)
  • 收稿日期:2006-06-26 修回日期:2006-02-21 发布日期:2007-05-10
  • 通讯作者: 许鹏飞

Synthesis of 3-Thioheterocycloyl-1,3,4,5-tetrahdro- 2-oxo-1H-benazepine

QIU Zao-Zaoa, ZHANG Huan-Huana, HUI Xin-Pinga, XU Peng-Fei*,a
WANG Qinb, DU Yu-Pingb, YANG Yangb   

  1. (a State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engi-neering,
    Lanzhou University, Lanzhou 730000)
    (b Life School, Lanzhou University, Lanzhou 730000)
  • Received:2006-06-26 Revised:2006-02-21 Published:2007-05-10
  • Contact: XU Peng-Fei

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以芳酰肼为原料, 合成了一系列3-巯基-5-芳基-1,2,4-三唑、2-巯基-5-芳基-1,3,4-噁二唑和2-巯基-5-芳 基-1,3,4-噻二唑, 并通过硫原子对3-溴-2-氧代-苯并氮杂3-位上的亲核取代反应将杂环化合物引入了苯并氮杂的结构当中, 合成了32个新的苯并氮杂杂环衍生物. 为提高其在有机溶剂中的溶解性, 在苯并氮杂的N原子上引入乙酸乙酯和乙酸叔丁酯基取代基, 合成了36个新衍生物. 所有化合物经质谱、核磁共振谱及元素分析确证了结构并初步测定了抗菌活性.

关键词: 杂环化合物, 亲核取代反应, 抗菌活性, 苯并氮杂

3-Thiol-1,2,4-triazole, 2-thiol-1,3,4-oxadiazole and 2-thiol-1,3,4-thiadiazole compounds were synthesized from hydrazides through different ways. By the nucleophilic substitution of S for Br on 3-bromo-1,3,4,5-tetrahydro-2-oxo-1H-benazepine, 32 derivatives of tetrahy-dro-2-oxo-1H-benazepine were synthesized. In order to improve dissolving ability in organic sol-vents, other 36 derivatives, which have a substituent of acetate on the 1-N position of benazepine, were also prepared. The structures of these compounds were confirmed by MS, 1H and 13C NMR spectra and elemental analysis. The primary antibacterial activity test indicated that some of the com-pounds were effective against Bacillus subtilis, Staphylococcus aureus, Escherichia coli, Streptococcus and Candida albicans.

Key words: heterocyclic compound, nucleophilic substitution, antibacterial activity, benazepine