Asymmetric Synthesis and Antibacterial Activity of Chiral 2-Methoxycarbonyl-4-fluorophenyl-1, 5-benzothiazepines

作者：Mu Boshuai; Chang Suna; Bian Yanqing^*; Li Yuan^*

来源：Chemical Journal of Chinese Universities, 2017, 38(3): 413-420.

DOI：10.7503/cjcu20160546

• 1,5-Benzothiazepine
• Antifungal activity
• Asymmetric synthesis
• Chiral auxiliariy

The synthetic route was confirmed via the study of introduction or removing chiral auxiliary (R)-4-phenyl-2-oxazolidinone and optimizing reaction conditions. Eighteen optically active 1,5-benzothiazepines were synthesized under the chiral induction of (S) / (R)-4-benzyl-2-oxazolidinone and characterized by H-1 NMR, C-13 NMR, IR and HRMS. The relative configuration of compound 9h was validated by X-ray diffraction analysis. The e.e. values of the products were analyzed by HPLC. The antifungal activities of compounds were screened using the disk diffusion method against C. neoformans. The compounds which were synthesized with S-4-benzyl-2-oxazolidinone had high antibacterial effects against C. Neoformans. By contrast, the compounds which were synthesized with R-4-benzyl-2-oxazolidinone and racemic compounds had lower antibacterial effects. Moreover, The MIC and MFC values of the highly biological compounds 14a-14f were lower than those of fluconazole.

• 出版日期2017-3-10
• 单位河北师范大学