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Synthesis, Structure and H+/K+-ATPase Inhibitory Activity of Novel Triazolyl Substituted Tetrahydrobenzofuran Derivatives via One-pot Three-component Click Reaction |
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| Authors: | Hubiao Fang Lei Jin Nianyu Huang Junzhi Wang Kun Zou Zaigang Luo |
| Affiliation: | 1. Hubei Key Laboratory of Natural Products Research and Development, College of Chemistry and Life Sciences,China Three Gorges University, Yichang, Hubei 443002, China 2. Hubei Key Laboratory of Natural Products Research and Development, College of Chemistry and Life Sciences,China Three Gorges University, Yichang, Hubei 443002, China ; Hubei Tujia Institute of Medicine, China Three Gorges University, Yichang, Hubei 443002, China 3. College of Chemical Engineering, Anhui University of Science & Technology, Huainan, Anhui 232001, China |
| Abstract: | 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. |
| Keywords: | tetrahydrobenzofuran three-component click reaction H+/K+-ATPase inhibitor X-ray diffraction analysis synthesis |
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