Quinoline-based imidazole-fused heterocycles as new inhibitors of 15-lipoxygenase

Abstract

A series of 2-chloro-quinoline-based imidazopyridines 6a–l and imidazothiazoles 6m–o bearing a bulky alkylamine side chain were synthesized as soybean 15-LOX inhibitors. The target compounds 6a–o were prepared via one-pot reaction of 2-chloroquinoline-3-carbaldehyde (3), heteroaromatic amidine 4, and alkyl isocyanides 5, in the presence of NH₄Cl. All compounds showed significant anti-15-LOX activity (IC₅₀ values ≤40 μM). Among the title compounds, the imidazo[2,1-b]thiazole derivative 6n bearing a tert-butylamine moiety showed the highest activity against soybean 15-LOX enzyme.

Keywords:

• Docking study
• enzyme inhibitors
• 15-lipoxygenase
• imidazo[1,2-a]pyridine
• imidazo[2,1-b]thiazole

Declaration of interest

The authors report no declarations of interest. This work was supported and funded by Research council of Tehran University of Medical Sciences (TUMS); Grant no: 95-01-92-31756; and Iran National Science Foundation (INSF).

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