Synthesis and in vitro antiproliferative activity against human cancer cell lines of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-diones
- First Online:
- Cite this article as:
- Chandrappa, S., Benaka Prasad, S.B., Vinaya, K. et al. Invest New Drugs (2008) 26: 437. doi:10.1007/s10637-008-9130-7
A series of novel 5-(4-methyl-benzylidene)-thiazolidine-2,4-dione derivatives 6 (a–d) and 7 (a–g) were synthesized with different substituted aromatic sulfonyl chlorides (R–SO2–Cl) and alkyl halides (R–X) and were characterized by 1H NMR, LC/MS, FTIR and elemental analyses. All the compounds synthesised were evaluated for their cell antiproliferation activity by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. The antiproliferative effects of the synthesised compounds were tested against viable human skin fibroblast cell line and carcinoma cell lines namely HeLa cells, HT-29 cells, MCF-7 cells, HepG-2 cells by adopting positive and negative control. The importance of the nitro group on thiazolidinone moiety was confirmed and it was concluded that the fourth position of the substituted aryl ring plays a dominant role and was responsible for the antiproliferative activity. Among the synthesized compounds only 6a, 7e and 7g have potent antiproliferative activity on all the carcinoma cell lines tested.