Synthesis of MMP inhibitor radiotracers [11C]methyl-CGS 27023A and its analogs, new potential PET breast cancer imaging agents

[C-11]Methyl-CGS 27023A (1a) and its analogs [C-11]methyl-2-picolyl-CGS 27023A (1b), [C-11]methyl-benzyl-CGS 27023A (1c), [C-11]methyl-2-nitro-CGS 27023A (1d), [C-11]methyl-3-nitro-CGS 27023A (1e), and [C-11]methyl-4-nitro-CGS 27023A (1f), novel radiolabeled matrix metalloproteinase (MMP) inhibitors, have been synthesized for evaluation as new potential positron emission tomography (PET) breast cancer imaging agents. The appropriate precursors for radiolabeling were obtained in four to five steps from starting material amino acid D-valine with moderate to excellent chemical yields. Precursors were labeled by [C-11]methyl triflate through C-11-O-methylation method at the aminohydroxyl position under basic conditions and isolated by solid-phase extraction (SPE) purification to produce pure target compounds in 40-60% radiochemical yields (decay corrected to end of bombardment), in 20-25 min synthesis time. Copyright (C) 2002 John Wiley Sons, Ltd.