title: The MMP inhibitor (R)-2-(N-benzyl-4-(2-[18F]fluoroethoxy)phenylsulphonamido)-N-hydroxy-3-methylbutanamide: Improved precursor synthesis and fully automated radiosynthesis.
abstract: The CGS 25966 derivative (R)-2-(N-Benzyl-4-(2-[(18)F]fluoroethoxy)phenyl-sulphonamido)-N-hydroxy-3-methylbutanamide [(18)F]9 represents a very potent radiolabelled matrix metalloproteinase inhibitor. For first human PET studies it is mandatory to have a fully automated radiosynthesis and a straightforward precursor synthesis available. The realisation of both requirements is reported herein. In particular, the corresponding precursor 8 was obtained in a reliable 7 step synthesis with an overall chemical yield of 2.3%. Furthermore, the target compound [(18)F]9 was prepared with a radiochemical yield of 14.8±3.9% (not corrected for decay).
authors.affiliation: Department of Nuclear Medicine, University Hospital Münster, Germany. stwagner@uni-muenster.de
authors.forename: Stefan
authors.initials: S
authors.lastname: Wagner
authors.forename: Andreas
authors.initials: A
authors.lastname: Faust
authors.forename: Hans-Jörg
authors.initials: HJ
authors.lastname: Breyholz
authors.forename: Otmar
authors.initials: O
authors.lastname: Schober
authors.forename: Michael
authors.initials: M
authors.lastname: Schäfers
authors.forename: Klaus
authors.initials: K
authors.lastname: Kopka
mesh_terms: D005462:Fluorine Radioisotopes / Q000737:chemistry* / Q000378:metabolism; D006877:Hydroxamic Acids / Q000138:chemical synthesis*; D007553:Isotope Labeling; D020782:Matrix Metalloproteinases / Q000378:metabolism; D009842:Oligopeptides / Q000138:chemical synthesis*; D049268:Positron-Emission Tomography / Q000379:methods*; D013449:Sulfonamides / Q000138:chemical synthesis*
chemical_list: C095170:4-aminobenzoyl-glycyl-prolyl-leucyl-alanine hydroxamic acid; D005462:Fluorine Radioisotopes; D006877:Hydroxamic Acids; C490459:N-hydroxy-2-(((4'-methoxyphenyl)sulfonyl)benzylamino)-3-methylbutanamide; D009842:Oligopeptides; D013449:Sulfonamides; D020782:Matrix Metalloproteinases