Synthesis to Access Tetrahydroprotoberberine-derived Benzimidazoles
作者单位：Laboratory of Bioorganic ＆ Medicinal ChemistrySchool of Chemistry and Chemical EngineeringSouthwest University
会议名称：《中国化学会第十三届全国有机合成化学学术研讨会》
会议日期：2016年
学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学]
基 金：partially supported by National Natural Science Foundation of China[(No.21372186,21672173) the Research Fund for International Young Scientists from International(Regional) Cooperation and Exchange Program(No.81650110529)] Chongqing Special Foundation for Postdoctoral Research Proposal(Xm2015031)
关 键 词：berberine benzimidazole antibacterial antifungal MRSA
摘 要：Tetracyclic tetrahydroprotoberberines（THPB） alkaloids contain an isoquinoline backbone and was endowed with various biological properties such as analgesic,anti-convulsant,anti-depressant and anti-psychotic abilities in the central nervous *** the rapid progress of science,the treatment of infectious diseases still remains a serious problem to the scientific community.A key intermediate containing an aldehyde group at 12-position of tetrahydroprotoberberrubine was developed for future *** aldehyde is easy to be attacked by neucleophilic reagents to access a series of berberrubine modified benzimidazole derivatives that can ameliorate the weakness of *** 1 H-NMR spectra of ±-Tetrahydroprotoberberrubine-12-（4-flurobenzyl-benzimidazole） in DMSO-d6 indicated the appearance of –OH proton（1 singlet at 9.17 ppm）.Two doublet at 7.67,7.58 ppm and one multiplets at 7.28 – 7.22 ppm integrating 1 H,1 H and 2 H respectively for benzimidazole *** triplet at 7.08 ppm,one doublet of doublet at 7.00 ppm and two doublets at 5.40（d,J = 16.3 Hz,1 H）,and 5.24（d,J = 16.2 Hz,1 H）（geminal coupling） integrating 2 H,2 H,1 H,1 H respectively for aromatic benzyl group.