Synthesis and in vitro antiproliferative profile of novel isomeric aza-analogues of natural jaspine B

Abstract

A successful strategy for the construction of novel isomeric aza-analogues 13. HCl and 14. HCl of natural jaspine B was developed by constructing a vicinal diamino motif via a sequential Overman rearrangement, followed by a pyrrolidine core formation through SN2 type cyclisation. The olefin cross metathesis reaction was selected to incorporate the alkyl side chain unit. Based on an antiproliferative/cytotoxic evaluation study, it was observed that the final products display significant potency on Jurkat and HeLa cell lines, with IC50 values in the low micromolar range.