posted on 2024-02-26, 19:35authored bySubrata Roy, Shailesh Budhathoki, Ahmed D. Iqbal, Alexander N. Erickson, Mohamad Akbar Ali, Mohammad Abrar Alam
An
efficient synthesis of 3-amino-2-formyl-functionalized benzothiophenes
by a domino reaction protocol and their use to synthesize a library
of novel scaffolds have been reported. Reactions of ketones and 1,3-diones
with these amino aldehyde derivatives formed a series of benzothieno[3,2-b]pyridine and 3,4-dihydro-2H-benzothiopheno[3,2-b]quinolin-1-one, respectively. A plausible mechanism for
the formation of fused pyridine derivatives by the Friedlander reaction
has been elucidated by density functional theory (DFT) calculations.
Furthermore, hydrazones were obtained by reacting the aldehyde functional
group of benzothiophenes with different hydrazine derivatives. Preliminary
screening of these compounds against several bacterial strains and
cancer cell lines led to the discovery of several hit molecules. Hydrazone
and benzothieno[3,2-b]pyridine derivatives are potent
cytotoxic and antibacterial agents, respectively. One of the potent
compounds effected ∼97% growth inhibition of the LOX IMVI cell
line at 10 μM concentration.