A Re(V)-catalyzed C-N bond-forming route to human lipoxygenase inhibitors.
[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.
Ohri
Rachana V
RV
Department of Chemistry and Biochemistry, University of California-Santa Cruz, Santa Cruz, California, USA.
Radosevich
Alexander T
AT
Hrovat
K James
KJ
Musich
Christine
C
Huang
David
D
Holman
Theodore R
TR
Toste
F Dean
FD
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
D016859:Lipoxygenase Inhibitors; D009942:Organometallic Compounds; D011437:Propylamines; D011758:Pyrroles; C094409:pentabromopseudilin; C009054:propargylamine; D012211:Rhenium; D010293:Pargyline