手性2-甲氧羰基-4-氟苯基-1,5-苯并硫氮杂卓的不对称合成及抑真菌活性

发布时间：2018-03-13 02:21

本文选题：-苯并硫氮杂卓　切入点：抑真菌活性　出处：《高等学校化学学报》2017年03期 　论文类型：期刊论文

【摘要】：以(R)/(S)-4-苄基-2-VA唑烷酮为手性助剂,采用不对称合成方法制备了18个具有光学活性的2-甲氧羰基-4-氟苯基-1,5-苯并硫氮杂卓类化合物9a~9i和14a~14i,经HPLC分析e.e.值较为理想;通过核磁共振谱、红外光谱和高分辨质谱表征了其结构,通过单晶X射线衍射法确定化合物9h的相对构型;用抑菌圈法测试了目标化合物对新生隐球菌的抑菌活性.研究结果表明,由S型手性助剂诱导不对称合成的杂卓对新生隐球菌的抑制作用普遍高于由R型手性助剂诱导合成的杂卓及外消旋体.测试了抑菌活性较好的化合物14a~14f的最小抑菌浓度(MIC)和最小杀菌浓度(MFC),发现其对新生隐球菌的MIC和MFC均低于抗真菌药物氟康唑.
[Abstract]:In (R) / (S) -4- benzyl -2-VA as oxazolidinone chiral auxiliary, preparation of 18 optically active 2- fluorenylmethoxycarbonyl -4- difluorophenyl -1,5- benzothiazepine compounds 9a~9i and 14a~14i by using the method of asymmetric synthesis, HPLC analysis of E.E. value ideal; by nuclear magnetic resonance spectroscopy, infrared spectroscopy high resolution mass spectrometry and characterization of its structure, determine the relative configuration of the compound 9h by single crystal X ray diffraction method; the antibacterial activity of the target compounds of Cryptococcus neoformans test by the bacteriostatic circle method. The results show that the inhibition of S induced by chiral auxiliaries in asymmetric synthesis of miscellaneous Zhuo on Cryptococcus neoformans is generally higher than that by R type of chiral auxiliaries and racemic complex Zhuo induced synthesis. The minimal inhibitory concentration of compound 14a~14f has better antibacterial activity test (MIC) and minimum bactericidal concentration (MFC), on the discovery of Cryptococcus neoformans MIC and MFC were lower than that of anti really Fluconazole, a bacterial drug.

【作者单位】：河北师范大学化学与材料科学学院;河北师范大学生命科学学院;
【基金】：国家自然科学基金(批准号:20972040)资助~~
【分类号】：O621.3

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