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Quinoline-Based Imidazole-Fused Heterocycles As New Inhibitors of 15-Lipoxygenase Publisher Pubmed



Dianat S1 ; Moghimi S2 ; Mahdavi M3 ; Nadri H4 ; Moradi A4 ; Firoozpour L3 ; Emami S5 ; Mouradzadegun A1 ; Shafiee A2 ; Foroumadi A2, 3
Authors
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Authors Affiliations
  1. 1. Department of Chemistry, Faculty of Science, Shahid Chamran University, Ahvaz, Iran
  2. 2. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Drug Design and Development Research Center, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Department of Medicinal Chemistry, Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences, Yazd, Iran
  5. 5. Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center, Faculty of Pharmacy, Mazandaran University of Medical Sciences, Sari, Iran

Source: Journal of Enzyme Inhibition and Medicinal Chemistry Published:2016


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. © 2016 Informa UK Limited, trading as Taylor & Francis Group.