Synthesis of [19, 35, 36-(13)C(3)]-labeled TAK779 as a molecular probe.
Synthesis of [19, 35, 36-(13)C(3)]-labeled TAK779 as a molecular probe.
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合成[19,35,36-(13)C(3)]标记的TAK779作为分子探针。
DOI：
10.1016/j.bmc.2009.07.026
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发表时间：
2009
影响因子：
3.5
通讯作者：
Akaji,Kenichi
中科院分区：
文献类型：
--
作者：
Konno,Hiroyuki;Aimoto,Saburo;Smith,StevenO;Nosaka,Kazuto;Akaji,Kenichi
N，N-二甲基-N-[4-[2-（4-甲基苯基）-6，7-二氢-5H-苯并环庚烯-8-基]羰基]氨基]苄基]四氢-2H-吡喃-4-氯化铵（TAK 779）是一种有效的选择性非肽类CCR 5拮抗剂。为了使用位点特异性标记形式作为分子探针，制备在C19、35和36位含有13 C的TAK 779。市售的[13 C]-碘甲烷用于标记。从不含标记碳的已知羧酸片段开始，通过Suzuki-Miyaura反应连续偶联[13 C]-标记的甲苯基硼酸酯和通过酰胺键形成偶联[13 C]-标记的苯胺片段来构建标记的TAK 779。
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 containing13C at positions C19, 35, and 36 was produced. A commercially available [13C]-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 [13C]-labeled tolyl boronic ester by the Suzuki–Miyaura reaction and a [13C]-labeled aniline segment by amide bond formation.