Synthesis and biological evaluation of 2, 4-thiazolidinedione incorporated imidazo[1, 2-a] pyridines

Gayatri Devi B; Saisree K.; Sikender M; Madhava Reddy B.; Harinadha Babu V

Abstract

Synthesis and biological evaluation of 2, 4-thiazolidinedione incorporated imidazo[1, 2-a] pyridines

Author(s): Gayatri Devi B, Saisree K., Sikender M, Madhava Reddy B. and Harinadha Babu V

Codensation of different phenacyl bromides with 2-amino pyridine afforded 2–aryl imidazo(1,2-a) pyridines 1(a-e) . Vilsmeier-Haack reaction of 1(a-e) gave 2–aryl imidazo (1,2-a) pyridine -3-carbaldehydes 2(a-e). Further, the condensation of these carbaldehydes with thiazolidinedione in glacial acetic acid gave (5-{[2-aryl imidazo [1,2- a]pyridine-3-yl]methylidene}-1,3-thiazolidine-2,4-diones 3(a-e) in good yields. The structures of the synthesized compounds were confirmed on the basis of spectral data and the compounds were screened for in vitro anti cancer activity and in vivo anti-inflammatory activity. Compound 4d exhibited superior activity against MCF-7 and HCT- 116 cell lines at IC50 values of 14.02 and 18.12 μM. However, compound 4b showed slightly less activity against MCF-7 and HCT-116 cell lines with IC50 values of 22.8 and 24.0 μM. In antiinflammatory screening, compound 4c exhibited maximum activity and the results are comparable with the standarad drug, ibuprofen.

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