Synthesis of N‐(3‐azido‐4‐chlorophenyl)‐N′‐[<sup>3</sup>H‐methyl] thiourea, an efficient photoaffinity probe for the urea carrier

DOI Web Site Web Site 被引用文献1件

書誌事項

公開日
1994-03
権利情報
  • http://onlinelibrary.wiley.com/termsAndConditions#vor
DOI
  • 10.1002/jlcr.2580340312
公開者
Wiley

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<jats:title>Abstract</jats:title><jats:p>Starting from commercial 4‐chloro‐3‐nitroaniline, through a 5 step synthesis, was prepared 3‐azido‐4‐chlorophenylisothiocyanate <jats:bold>5</jats:bold> which was reacted with [<jats:sup>3</jats:sup>H]‐methylamine. The latter was obtained by three methods: <jats:list list-type="explicit-label"> <jats:list-item><jats:p>[<jats:sup>3</jats:sup>H]‐LiAlT<jats:sub>4</jats:sub> reduction of benzylcarbamate gave rise to [<jats:sup>3</jats:sup>H]‐methylamine (S.A.: >70 Ci/mmol).</jats:p></jats:list-item> <jats:list-item><jats:p>Catalytic reduction of HCN with <jats:sup>3</jats:sup>H<jats:sub>2</jats:sub> lead to [<jats:sup>3</jats:sup>H]‐CH<jats:sub>3</jats:sub>NH<jats:sub>2</jats:sub> (S.A.: 0.7 Ci/mmol).</jats:p></jats:list-item> <jats:list-item><jats:p>Schmidt rearrangement of [<jats:sup>3</jats:sup>H]‐sodium acetate gave [<jats:sup>3</jats:sup>H]‐CH<jats:sub>3</jats:sub>NH<jats:sub>2</jats:sub> (S.A.: 29 Ci/mmol).</jats:p></jats:list-item> </jats:list></jats:p><jats:p>Compound 7 at the highest specific activity had a self radiolysis rate precluding its practical use in biological studies whilst 29 Ci/mmol [<jats:sup>3</jats:sup>H]‐7 was satisfactory.</jats:p>

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