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Green multicomponent approach to diphenyl ether-connected bis-heterocycles: biological evaluation and their computational studies
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DOI：10.1186/s13065-026-01894-y.png)
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Abstract
En 中文
Bacterial resistance to currently available antibiotics underscores the urgent necessity for the innovation of novel anti-bacterial agents characterised by distinct mechanisms of action. In the current study, a series of dihydropyrano [2,3-d]carbonitriles and 4 H-pyran-3-carbonitrile/carboxylate derivatives, featuring ether-linked symmetrical and unsymmetrical bis-heterocyclic frameworks, were synthesised and subsequently subjected to a thorough assessment of their anti-bacterial efficacy against selected bacterial strains. In this regard, a highly efficient and environmentally sustainable one-pot procedure was devised utilising 4,4′-oxydibenzaldehyde, malononitrile, and active methylene compounds (including Meldrum’s acid, diethyl malonate, and 2,4-pentanedione) in ethanol, employing PEG-400 as a green catalytic agent. This methodology yielded symmetrical and unsymmetrical bis-heterocyclic systems through the Michael reaction interconnected via a diphenyl ether core in commendable yields under mild experimental conditions. Spectroscopic analyses confirmed the structures of the synthesised compounds. Several derivatives exhibited promising anti-bacterial and anti-oxidant activity, and the anti-bacterial potential was further validated through MIC and MBC determination. MIC and MBC evaluation suggest moderate anti-bacterial potential and predominantly bacteriostatic behavior against E. coli and B. subtilis strains. A molecular docking study against the membrane protein of E. coli (E. coli K12) revealed compound 8a showing the highest binding affinity, correlating with its high anti-bacterial activity. The pharmacokinetics, drug-likeness and physicochemical properties were estimated by SwissADME software.
Keywords:
Bis-heterocycles
PEG-400
Green catalyst
Anti-bacterial
Anti-oxidant
DFT
Docking
ADME
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