Synthesis and anti-leukemic activity of pyrrolidinedione-thiazolidinone hybrids

Abstract

A series of novel 2-(5-ylidene-4-oxo-2-thioxo-thiazolidin-3-yl)-succinimides and 5-ylidene-3-(1-arylpyrrolidine-2,5-dione)-thiazolidine-2,4-diones were synthesized. An efficient simple protocol for rhodanine-pyrrolidinedione hybrids synthesis which allows avoiding the step of anhydride formation was proposed. Following the previous data on antileukemic properties of related thiazolidinone derivatives, the activity of 19 target compounds was investigated towards four leukemia cell lines: Dami, HL-60, Jurkat, and K562. Among the tested compounds, 3-[5-(4-chloro-benzylidene)-4-oxo-2-thioxo-thiazolidin-3-yl]-1-phenyl-pyrrolidine-2,5-dione (Compound 1) possessed good and selective antiproliferative action against Dami and HL-60 cell lines and satisfactory toxicity level (acute toxicity evaluated in vivo in mice).

Keywords

• 4-thiazolidinone
• anti-leukemic activity
• anticancer activity
• pyrrolidinedione