(2’-溴-6’-(乙氧基甲基)-3’,4’-二甲氧基-苯基)-(2,3-二溴-4,5-二甲氧基-苯基)-甲酮

Synthesis and PTP1B inhhibitory activity investigation of (2’-bromo-6’-(ethoxymethyl)-3’,4’-dimethoxy-phenyl) -(2,3-dibromo-4,5-dimethoxy-phenyl)-methanone

摘要:

为了寻找新型的PTP1B酶抑制剂，以香兰素(1)为起始原料，经过溴代、傅克酰基化及亲核取代等7步反应，合成了化合物[2´-溴-6´-(乙氧基甲基)-3´,4´-二甲氧基-苯基]-(2,3-二溴-4,5-二甲氧基-苯基)-甲酮(8)，总收率为21.9%。通过1H-NMR、13C-NMR谱及红外光谱对目标产物进行了结构表征。采用比色法对化合物8进行了protein tyrosine phosphatase 1B (PTP1B)酶抑制活性测定，结果显示该化合物有一定的PTP1B酶抑制活性（化合物浓度为20mg •L-1时，PTP1B酶抑制率为73.83%）。

Abstract:

In order to search a novel PTP1B inhibitor, [2´-bromo-6´-(ethoxymethyl)-3´,4´-dimethoxy-phenyl]-(2,3-dibromo-4,5-dimethoxy-phenyl)-methanone 8 was synthesized in 7 steps with an overall yield of 21.9%, employing bromination, Friedel-Crafts reaction and nucleophilic substitution reaction as key steps. The structure of compound 8 was determined by 1H-NMR, 13C-NMR and infrared absorption spectra. Compound 8 was screened against protein tyrosine phosphatase 1B (PTP1B) with the colorimetric assay. The result indicated that compound 8 displayed good inhibitory activity against PTP1B (Inhibition 73.83% at 20 mg •L-1).