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A new series of substituted ethyl 7-cyclopropyl-2-(2-aryloxo)-3-nitro-4-oxo-4,7-dihydrothieno[2,3- b ]pyridine-5-carboxylates 3a – e were prepared by utilizing ethyl 2-chloro-7-cyclopropyl-3-nitro-4-oxo-4,7-dihydrothieno[2,3- b ]pyridine-5-carboxylate ( 1 ) and replacing of the 2-chlorine with anions obtained from phenol ( 2a ), salicylaldehyde derivatives 2b – d or thiophenol ( 2e ), leading to the respective ethyl 7-cyclopropyl-2-(2-aryloxo)-3-nitro-4-oxo-4,7-dihydrothieno[2,3- b ]pyridine-5-carboxylates 3a – e . The new compounds were evaluated for their in vitro cytotoxicity towards sensitive CCRF-CEM and multidrug-resistant CEM/ADR5000 leukemia cells. The screening revealed that compounds 3a , 3b , and 3e inhibited the growth of both cell lines. Compound 3b , with a phenol moiety, exhibited the highest growth inhibitory activity against CEM/ADR5000 and CCRF-CEM cells with IC 50 values 4.486 ± 0.286 and 2.580 ± 0.550 µM, respectively. Collectively, the presented results demonstrate that the synthesized thieno[2,3- b ]pyridines warrant further exploration for potential use as anti-cancer agents.

Synthesis and Cytotoxicity of Thieno[2,3-b]Pyridine Derivatives Toward Sensitive and Multidrug-Resistant Leukemia Cells