title: Diastereoselective ruthenium porphyrin-catalyzed tandem nitrone formation/1,3-dipolar cycloaddition for isoxazolidines. Synthesis, in silico docking study and in vitro biological activities.
abstract: Ruthenium porphyrin catalyzes tandem nitrone formation/1,3-dipolar cycloaddition of diazo compounds, nitrosoarenes and alkenes to form isoxazolidines in good to high yields and with excellent regio-, chemo- and diastereo-selectivities. A broad substrate scope of alkenes is applicable to this protocol and various functional groups are compatible with the reaction conditions. In silico analysis and in vitro biological experiments revealed that some of the new isoxazolidines synthesized in this work could act as leukotriene A4 hydrolase inhibitors.
authors.affiliation: Department of Chemistry, State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China.
authors.forename: Annapureddy Rajasekar
authors.initials: AR
authors.lastname: Reddy
authors.forename: Zhen
authors.initials: Z
authors.lastname: Guo
authors.forename: Fung-Ming
authors.initials: FM
authors.lastname: Siu
authors.forename: Chun-Nam
authors.initials: CN
authors.lastname: Lok
authors.forename: Fuli
authors.initials: F
authors.lastname: Liu
authors.forename: Kai-Chung
authors.initials: KC
authors.lastname: Yeung
authors.forename: Cong-Ying
authors.initials: CY
authors.lastname: Zhou
authors.forename: Chi-Ming
authors.initials: CM
authors.lastname: Che
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D001665:Binding Sites; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D003500:Cyclization; D061565:Cycloaddition Reaction; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D004851:Epoxide Hydrolases / Q000037:antagonists & inhibitors; D006801:Humans; D007555:Isoxazoles / Q000138:chemical synthesis*; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000138:chemical synthesis*; D011166:Porphyrins / Q000737:chemistry*; D011485:Protein Binding; D011994:Recombinant Proteins / Q000037:antagonists & inhibitors; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D001391:Azo Compounds; D056831:Coordination Complexes; D004791:Enzyme Inhibitors; D007555:Isoxazoles; D009589:Nitrogen Oxides; D011166:Porphyrins; D011994:Recombinant Proteins; C015388:nitrones; D012428:Ruthenium; D004851:Epoxide Hydrolases; C043134:leukotriene A4 hydrolase