A 1,4-Diphenyl-1,2,3-Triazole-Based β-Turn Mimic Constructed by Click Chemistry

A series of 1,4-diphenyl-1,2,3-triazole-incorporated
amide derivatives
have been designed and prepared. X-ray crystallographic and (1D and
2D) 1H NMR studies reveal that these compounds fold into
stable U-shaped conformations driven by three-center intramolecular
C–H···O hydrogen-bonding formed between the
triazole C-5 H atom and the two ether O atoms. Such folded structures
make this 1,4-diphenyl-1,2,3-triazole skeleton a good candidate to
be used as β-turn mimic. To prove this, the formation of a β-hairpin
structure induced by this β-turn motif has been further demonstrated.