title: A Re(V)-catalyzed C-N bond-forming route to human lipoxygenase inhibitors.
abstract: [reaction: see text] A regioselective synthesis of propargylamines by the coupling of propargyl alcohols with tosylamines and carbamates catalyzed by an air- and moisture-tolerant rhenium-oxo complex is described. The ability to couple functionalized components allows for convergent approaches to nitrogen-containing heterocyclic compounds such as the marine antibiotic pentabromopseudilin. These compounds were assayed against human lipoxygenase and found to be both potent and selective.
authors.affiliation: Department of Chemistry and Biochemistry, University of California-Santa Cruz, Santa Cruz, California, USA.
authors.forename: Rachana V
authors.initials: RV
authors.lastname: Ohri
authors.forename: Alexander T
authors.initials: AT
authors.lastname: Radosevich
authors.forename: K James
authors.initials: KJ
authors.lastname: Hrovat
authors.forename: Christine
authors.initials: C
authors.lastname: Musich
authors.forename: David
authors.initials: D
authors.lastname: Huang
authors.forename: Theodore R
authors.initials: TR
authors.lastname: Holman
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
mesh_terms: D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006801:Humans; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis* / Q000378:metabolism; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011437:Propylamines / Q000138:chemical synthesis*; D011758:Pyrroles / Q000737:chemistry / Q000494:pharmacology*; D012211:Rhenium / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D016859:Lipoxygenase Inhibitors; D009942:Organometallic Compounds; D011437:Propylamines; D011758:Pyrroles; C094409:pentabromopseudilin; C009054:propargylamine; D012211:Rhenium; D010293:Pargyline