title: 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 (IC50values ≤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.
authors.affiliation: a Department of Chemistry , Faculty of Science, Shahid Chamran University , Ahvaz , Iran.
authors.forename: Shima
authors.initials: S
authors.lastname: Dianat
authors.affiliation: b Department of Medicinal Chemistry , Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences , Tehran , Iran.
authors.forename: Setareh
authors.initials: S
authors.lastname: Moghimi
authors.affiliation: c Drug Design and Development Research Center, Tehran University of Medical Sciences , Tehran , Iran.
authors.forename: Mohammad
authors.initials: M
authors.lastname: Mahdavi
authors.affiliation: d Department of Medicinal Chemistry , Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences , Yazd , Iran , and.
authors.forename: Hamid
authors.initials: H
authors.lastname: Nadri
authors.affiliation: d Department of Medicinal Chemistry , Faculty of Pharmacy, Shahid Sadoughi University of Medical Sciences , Yazd , Iran , and.
authors.forename: Alireza
authors.initials: A
authors.lastname: Moradi
authors.affiliation: c Drug Design and Development Research Center, Tehran University of Medical Sciences , Tehran , Iran.
authors.forename: Loghman
authors.initials: L
authors.lastname: Firoozpour
authors.affiliation: e Department of Medicinal Chemistry and Pharmaceutical Sciences Research Center , Faculty of Pharmacy, Mazandaran University of Medical Sciences , Sari , Iran.
authors.forename: Saeed
authors.initials: S
authors.lastname: Emami
authors.affiliation: a Department of Chemistry , Faculty of Science, Shahid Chamran University , Ahvaz , Iran.
authors.forename: Arash
authors.initials: A
authors.lastname: Mouradzadegun
authors.affiliation: b Department of Medicinal Chemistry , Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences , Tehran , Iran.
authors.forename: Abbas
authors.initials: A
authors.lastname: Shafiee
authors.affiliation: b Department of Medicinal Chemistry , Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences , Tehran , Iran.|c Drug Design and Development Research Center, Tehran University of Medical Sciences , Tehran , Iran.
authors.forename: Alireza
authors.initials: A
authors.lastname: Foroumadi
mesh_terms: D001093:Arachidonate 15-Lipoxygenase / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007093:Imidazoles / Q000737:chemistry / Q000494:pharmacology*; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D015394:Molecular Structure; D011804:Quinolines / Q000737:chemistry / Q000494:pharmacology*; D013025:Glycine max / Q000201:enzymology; D013329:Structure-Activity Relationship
chemical_list: D006571:Heterocyclic Compounds; D007093:Imidazoles; D016859:Lipoxygenase Inhibitors; D011804:Quinolines; C029899:imidazole; C037219:quinoline; D001093:Arachidonate 15-Lipoxygenase
keywords: 15-lipoxygenase; Docking study; enzyme inhibitors; imidazo[1,2-a]pyridine; imidazo[2,1-b]thiazole