Synthesis of [19, 35, 36-(13)C(3)]-labeled TAK779 as a molecular probe.
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.
Konno
Hiroyuki
H
Department of Chemistry, Kyoto Prefectural University of Medicine, Kita-ku, Japan.
Aimoto
Saburo
S
Smith
Steven O
SO
Nosaka
Kazuto
K
Akaji
Kenichi
K
D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D065100:CCR5 Receptor Antagonists; D002250:Carbon Radioisotopes / Q000737:chemistry*; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D015335:Molecular Probes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D019713:Receptors, CCR5 / Q000378:metabolism
D000577:Amides; D065100:CCR5 Receptor Antagonists; D002250:Carbon Radioisotopes; D006847:Hydrocarbons, Iodinated; D015335:Molecular Probes; D000644:Quaternary Ammonium Compounds; D019713:Receptors, CCR5; C119369:TAK 779; C014055:methyl iodide