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化学学报
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化学学报 ›› 2009, Vol. 67 ›› Issue (23): 2732-2738. 上一篇    下一篇

研究论文

C(3)-酯基取代的1,5-苯并硫氮杂卓的合成、晶体结构及抑菌和构效关系的研究

李文红c，兰佳明b，李成a，曹云涛a，王海波a，王兰芝a，张萍a，王永祥*,b，李 媛*,a   

  1. (a河北师范大学化学与材料科学学院 石家庄 050016) (b河北医科大学病原生物学部 石家庄 050017) (c河北工业职业技术学院环境与化学工程系 石家庄 050091)
  • 投稿日期:2009-05-01 修回日期:2009-07-21 发布日期:2009-08-10
  • 通讯作者: 李媛 E-mail:yuanli@mail.hebtu.edu.cn

Synthesis, Crystal Structure, Antimicrobial Activity and Structure Activity Relationship of 3-Ethoxycarbonyl-1,5-benzothiazepines

Li, Wenhongc，Lan, Jiamingb，Li, Chenga，Cao, Yuntaoa，Wang, Haiboa ，Wang, Lanzhia，Zhang, Pinga，Wang, Yongxiang*,b，Li, Yuan*,a   

  1. (a College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050016) (b Department of Pathogenic Biology, Hebei Medical University, Shijiazhuang 050017) (c Environment and Chemical Engineering, Heibei College of Industry and Technology, Shijiazhuang 050091)
  • Received:2009-05-01 Revised:2009-07-21 Published:2009-08-10

PDF

1462

被引次数

19

设计、合成了三类C(3)酯基取代的1,5-苯并硫氮杂卓衍生物: 2,3/2,5-二氢和2,3,4,5-四氢-1,5-苯并硫氮杂卓-3-甲酸乙酯, 采用元素分析、IR、MS、1H NMR及X射线衍射法确定了标题化合物的分子结构．结构分析表明, 2,5-二氢-1,5-苯并硫氮杂卓-3-甲酸乙酯属单斜晶系, C2/c空间群, 晶胞参数为: a＝2.0319(4) nm, b＝1.4985(3) nm, c＝1.3659(3) nm, α＝90°, β＝120.49(3)°, γ＝90°, V＝3.5840(12) nm3, Z＝8, Dc＝1.397 g/cm3, μ＝0.351 mm－1, F(000)＝1560, R＝0.0478, Rw＝0.1304; 研究了2,3/2,5-二氢-1,5-苯并硫氮杂卓的合成反应条件, 发现该两种互变异构体分别是速度控制产物和平衡控制产物; 抑菌活性及抑真菌构效关系研究表明, 亚胺型的2,3-二氢-1,5-苯并硫氮杂卓具有明显的抑菌活性, 亚胺官能团是其抑真菌的药效团．

关键词: 1,5-苯并硫氮杂卓, 速度控制产物, 平衡控制产物, 抑菌活性, 构效关系

Three kinds of 3-ethoxycarbonyl-1,5-benzothiazepines were designed, synthesized and structurally confirmed by elemental analysis, IR, 1H NMR, MS and X-ray diffraction. The crystal of compound 5b belongs to monoclinic, space group C2/c with unit cell dimensions a＝2.0319(4) nm, b＝1.4985(3) nm, c＝1.3659(3) nm, α＝90°, β＝120.49(3)°, γ＝90°, V＝3.5840(12) nm3, Z＝8, Dc＝1.397 g/cm3, μ＝0.351 mm－1, F(000)＝1560, R＝0.0478, and Rw＝0.1304. Studies on the synthesis conditions of 2,3/2,5-dihydro-1,5-benzothiazepines revealed that 2,3/2,5-dihydro-1,5-benzothiazepines that are imine-enamine tautomers were speed control and balance control products respectively. The biological evaluation of those compounds showed that 1,5-benzothiazepines with C＝N group had moderate to excellent antimicrobial activities and the C＝N double bond in the newly synthesized compounds was the key function group for their antifungal activities.

Key words: 1,5-benzothiazepine, speed control product, balance control product, antibacterial activity, structure-activity relationship