Bioorganic & Medicinal Chemistry 2009-08-15

Synthesis of [19, 35, 36-(13)C(3)]-labeled TAK779 as a molecular probe.

Hiroyuki Konno, Saburo Aimoto, Steven O Smith, Kazuto Nosaka, Kenichi Akaji

Index: Bioorg. Med. Chem. 17(16) , 5769-74, (2009)

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Abstract

N,N-Dimethyl-N-[4-[[[2-(4-methylphenyl)-6,7-dihydro-5H-benzocyclohepten-8-yl]carbonyl]amino]benzyl]tetrahydro-2H-pyran-4-aminium chloride (TAK779) is a potent and selective non-peptide CCR5 antagonist. To use a site-specifically labeled form as a molecular probe, TAK779 containing (13)C at positions C19, 35, and 36 was produced. A commercially available [(13)C]-methyl iodide was employed for the labeling. Starting from a known carboxylic acid segment containing no labeled carbon, the labeled TAK779 was constructed by the successive coupling of [(13)C]-labeled tolyl boronic ester by the Suzuki-Miyaura reaction and a [(13)C]-labeled aniline segment by amide bond formation.