Synthesis, Structure and H+/K+-ATPase Inhibitory Activity of Novel Triazolyl Substituted Tetrahydrobenzofuran Derivatives via One-pot Three-component Click Reaction

Eleven triazolyl substituted tetrahydrobenzofuran derivatives were synthesized in high yields as novel H+/K+-ATPase inhibitor via one-pot CuI-catalyzed three-component click reaction of azide, secondary amine and 3-bromopropyne under mild conditions in water. Their structures were characterized by NMR, IR, ESI-MS, elemental analysis and single-crystal X-ray diffraction analysis. Most of the target compounds exhibited better H+/K+-ATPase inhibitory activity than commercial omeprazole with IC50 values less than 15 µmol·L−1. The initial structure-activity analysis suggested that the triazole substituted by cycloalkyl, aromatic ring or O-containing side-chain seemed to be beneficial for enhancing the activity.