title: Microwave-enhanced alpha-arylation of a protected glycine in water: evaluation of 3-phenylglycine derivatives as inhibitors of the tuberculosis enzyme, glutamine synthetase.
abstract: A microwave-enhanced, palladium-catalyzed protocol for the alpha-arylation of a protected glycine in neat water is described. This reaction proceeds rapidly, under non-inert conditions, to afford a range of phenylglycine derivatives in moderate to good yields. Based on this alpha-arylation, a number of aryl L-methionine-SR-sulfoximine (MSO) analogues were prepared and evaluated for their Mycobacterium tuberculosis glutamine synthetase (TB-GS) inhibitory activity.
authors.affiliation: Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, Biomedical Center, Box 574, SE- 751 23 Uppsala, Sweden.
authors.forename: Olof
authors.initials: O
authors.lastname: Lagerlund
authors.forename: Luke R
authors.initials: LR
authors.lastname: Odell
authors.forename: Sherry L
authors.initials: SL
authors.lastname: Mowbray
authors.forename: Mikael T
authors.initials: MT
authors.lastname: Nilsson
authors.forename: Wojciech W
authors.initials: WW
authors.lastname: Krajewski
authors.forename: Anneli
authors.initials: A
authors.lastname: Nordqvist
authors.forename: Anders
authors.initials: A
authors.lastname: Karlén
authors.forename: Mats
authors.initials: M
authors.lastname: Larhed
mesh_terms: D002384:Catalysis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D005974:Glutamate-Ammonia Ligase / Q000037:antagonists & inhibitors*; D005998:Glycine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006844:Hydrocarbons, Cyclic / Q000737:chemistry*; D008717:Methionine Sulfoximine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D008872:Microwaves; D008956:Models, Chemical; D009169:Mycobacterium tuberculosis / Q000201:enzymology*; D010165:Palladium / Q000737:chemistry; D014867:Water / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; D006844:Hydrocarbons, Cyclic; D014867:Water; D008717:Methionine Sulfoximine; D010165:Palladium; D005974:Glutamate-Ammonia Ligase; D005998:Glycine