Solid-phase parallel synthesis of 1,3-thiazole library adorned with dipeptidyl chains

Abstract

In this study, we report a solid-phase synthesis of 1,3-thiazole based peptidomimetic molecules. The key reaction step is dehydrative cyclization of thiourea resin intermediate with 2-bromo-1-(3-nitrophenyl) ethanone to afford 1,3-thiazole core with benzyl-nitro group attached. Further modification of the nitro group with peptide elongations yielded resin-bound N-benzyl-1,3-thiazole derivatives with short peptide chains at C4 and C5 positions. Cleavage from the resin delivered compounds in moderate yields. Synthesized compounds had high purities (>97%). (C) 2020 Elsevier Ltd. All rights reserved.