Synthesis and biological activities of some new thiazolidine derivatives containing pyrazole ring system

Abstract

Abstract As a part of systematic investigation of synthesis and biologically active compounds of thiazolidine (TZD) derivatives containing pyrazole ring system, several new pyrazole–TZD derivatives 8a , 8b , 8c , 8d and 9a , 9b , 9c , 9d have been synthesized. Compounds 8a , 8b , 8c , 8d were prepared from N ‐substituted TZDs 6a , 6b , 6c , 6d and 1 H ‐pyrazole‐4‐carboxaldehyde 7 by Knoevenagel‐type reaction. Treatment of 8a , 8b , 8c , 8d with sodium hydride at room temperature caused dimerization reaction to afford the corresponding spirocompounds 9a , 9b , 9c , 9d . All the synthesized compounds were characterized by spectroscopic analysis. In vitro , the synthesized compounds 8a , 8b , 8c , 8d and 9a , 9b , 9c , 9d were tested for their growth inhibitory activity in A549 lung cancer, B16F10 murine melanoma, and HeLa human uterine carcinoma cells and for their differentiation of 3T3‐L1 preadipocytes to adipocytes. The results showed that compound 8c possessed growth inhibitory effect of B16F10 cells (IC 50 = 27 μM) and compounds 9c , 9d had induction effect on the differentiation of 3T3‐L1 preadipocytes. J. Heterocyclic Chem., (2011).