Synthesis of 2-(methylsulfonyl)-5-(4-(methylsulfonyl) phenyl)-4-phenyl-1H-[5-¹⁴C]imidazole, a selective COX-2 inhibitor, via asymmetrical benzoins

Abstract

4,5-Diarylimidazoles labeled with carbon-14 in the 5-position of the imidazole ring were prepared as a part of three-step sequence from 2-hydroxy-1-(4-(methylthio)phenyl)-2-phenyl[1-(14) C]ethanone as a key synthetic intermediate which has been synthesized from potassium [(14) C]cyanide.

Recent developments in heterocycle labeling with carbon isotopes

“…After 3 additional steps, [ 14 C]‐ 31 was elaborated into the α ‐bromo‐carbonyl derivative [ 14 C]‐ 32. In the presence of sodium methoxide, [ 14 C]‐ 32 was further converted into the α ‐hydroxy‐carbonyl [ 14 C]‐ 32a ; then, the crude material was directly treated with NH 4 SCN in refluxing n ‐butanol, affording the labeled thiourea [ 14 C]‐ 33 with 46% of overall yield (Scheme 13).…”

Synthesis of (2-mercaptoacetyl)-L-[2-14C]tryptophan as a selective metallo-β-lactamase inhibitor via [2-14C]indole based on chiral pool strategy

“…To further clarify mechanism of action and specify pharmacological interaction, we find that synthesis of 14 C‐labeled (2‐mercaptoacetyl)‐L‐tryptophan was required. In this paper, we report continuation of our previous work on the synthesis of 14 C‐labeled inhibitors and, specifically, a convenient synthetic pathway for the preparation of compound d, (n = 1) in which 2‐position of indole ring was labeled with carbon‐14 (Scheme ).…”