Stereoselective synthesis and anticancer activity of broussonetine analogues |
| |
Authors: | Dominika Jacková Miroslava Martinková Jozef Gonda Mária Vilková Martina Bago Pilátová Peter Takáč |
| |
Institution: | 1. Institute of Chemical Sciences, Department of Organic Chemistry, Faculty of Science, P.J. ?afárik University, Moyzesova 11, 040 01 Ko?ice, Slovak Republic;2. Institute of Pharmacology, Faculty of Medicine, P.J. ?afárik University, SNP 1, 040 66 Ko?ice, Slovak Republic |
| |
Abstract: | The stereoselective synthesis of two broussonetine analogues 14·HCl and ent-14·HCl with differing stereochemistry of the polyhydroxylated pyrrolidine core and a simple C13 alkyl fragment has been achieved. For their construction, the known oxazolidinones 15 and 16 were chosen as appropriate advanced scaffolds. The common hydrophobic side chain was incorporated at an early stage of the synthesis through Grubbs’ cross metathesis chemistry. The required pyrrolidine skeleton was then formed by the cyclization of open chain intermediates 17 and 18. Four synthesized compounds were screened in vitro for antiproliferative/cytotoxic activity against six cancer cell lines by MTT assay. Compounds 14·HCl (HeLa and A-549) and ent-14·HCl (Caco-2 and Jurkat) showed comparable or higher potency than conventional anticancer agent cisplatin on at least two evaluated cancer cells, respectively. |
| |
Keywords: | Corresponding author Tel : +421 55 6222348 fax: +421 55 6222124 |
本文献已被 ScienceDirect 等数据库收录! |
|