Synthesis and <i>in vitro </i>hypoglycemic activity of 3-(4′-benzoyl amino-phenyl)-coumarin derivatives

HU Yuheng; SUN Jie; YANG Jie; WANG Xiaojing

doi:10.11665/j.issn.1000-5048.20190206

Journal of China Pharmaceutical University > 2019 > 50(2): 168-174. > DOI: 10.11665/j.issn.1000-5048.20190206

HU Yuheng, SUN Jie, YANG Jie, WANG Xiaojing. Synthesis and in vitro hypoglycemic activity of 3-(4′-benzoyl amino-phenyl)-coumarin derivatives[J]. Journal of China Pharmaceutical University, 2019, 50(2): 168-174. DOI: 10.11665/j.issn.1000-5048.20190206

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Synthesis and in vitro hypoglycemic activity of 3-(4′-benzoyl amino-phenyl)-coumarin derivatives

HU Yuheng^1,2,3,4,
SUN Jie^1,2,3,4,
YANG Jie^1,2,3,4,
WANG Xiaojing^1,2,3,4

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Abstract

Firstly, three 3-arylcoumarins 4a- 4c were synthesized from p-aminophenylacetic acid and salicylaldehyde by Perkin condensation reaction and hydrochloric acid acidification; subsequent-amidation reaction of 4a- 4c with substituted benzoyl chlorides 6a - 6h furnished; ten 3-(4′-benzoyl amino-phenyl)coumarins 7a- 7j . The structures of all target compounds were fully characterised by NMR and ESI-MS. Those target compounds were screened for-glucosidase inhibitory and advanced glycation end products(AGEs)formation inhibitory activity. The results showed that compound 7f had good inhibitory activity against α-glucosidase(IC₅₀=10. 84±0. 36 μmol/L); compound 7g possessed much more potent inhibitory activity against AGEs formation(IC₅₀=5. 01±0. 55 μmol/L)than the positive control aminoguanidine hydrochloride(IC₅₀=290. 31±7. 32 μmol/L). These results provided a theoretical basis for further research on antidiabetic drugs.

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