新型酰基硫脲衍生物的合成及细胞分裂周期25B磷酸酶和蛋白酪氨酸磷酸酶1B抑制活性研究
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摘要
采用超声波辐射与固-液相转移催化联用技术合成出了一系列新型含咔唑基团的酰基硫脲衍生物3,利用IR、~1H NMR、~(13)C NMR和元素分析对其进行了结构表征.该合成方法具有反应时间短、操作简便、产率高等优点.对所合成的目标化合物进行了细胞分裂周期25B磷酸酶(Cdc25B)和蛋白酪氨酸磷酸酶1B(PTP1B)抑制活性筛选,实验结果显示,目标化合物3对Cdc25B均具有良好的抑制活性,部分化合物对PTP1B也表现出良好的抑制活性.其中1-(4-硝基苯甲酰基)-3-(9-乙基-咔唑-3-基)硫脲(3n)对Cdc25B的抑制活性最高[IC50=(0.49±0.12)mg/mL],1-(2-硝基苯甲酰基)-3-(9-乙基-咔唑-3-基)硫脲(3l)对PTP1B的抑制活性最高[IC50=(3.59±1.15)mg/m L].值得注意的是,化合物3n对Cdc25B和PTP1B均具有较高的抑制活性.分子对接的初步研究结果揭示了此类抑制剂的结构-活性关系.这些活性目标化合物是潜在的Cdc25B和PTP1B抑制剂,在癌症和糖尿病治疗方面具有很好的应用前景.
A series of new acylthiourea derivatives 3 containing carbazole moity have been synthesized by the techniques of ultrasonic irradiation and solid-liquid phase transfer catalysis.Their structures were characterized by IR,1 H NMR,13 C NMR spectra and elemental analysis.This synthetic method has the advantages of short reaction time,simple operation and high yield.All synthesized target compounds were screened for their inhibitory activity against cell division cycle 25 B phosphatase(Cdc25 B) and protein tyrosine phosphatase 1 B(PTP1 B).The results show that all the compounds 3 display significant inhibitory activities against Cdc25 B,and partial target compounds 3 also show significant inhibitory activities against PTP1 B.Among them,1-(4-nitrobenzoyl)-3-(9-ethyl-carbazole-3-yl)thiourea(3 n) exhibits highest inhibitory activity against Cdc25 B [IC50=(0.49±0.12) ?g/m L] and 1-(2-nitrobenzoyl)-3-(9-ethyl-carbazole-3-yl)thiourea(3 l) displays highest inhibitory activity against PTP1 B [IC50=(3.59±1.15) ?g/m L].It is noteworthy that compound 3 n shows higher inhibitory activity against Cdc25 B and PTP1 B.The preliminary research results of molecular docking revealed the structural-activity of the inhibitors.The active compounds can be considered as potential Cdc25 B and PTP1 B inhibitors,and have great application prospects in the treatment of cancers and diabetes.
A series of new acylthiourea derivatives 3 containing carbazole moity have been synthesized by the techniques of ultrasonic irradiation and solid-liquid phase transfer catalysis.Their structures were characterized by IR,1 H NMR,13 C NMR spectra and elemental analysis.This synthetic method has the advantages of short reaction time,simple operation and high yield.All synthesized target compounds were screened for their inhibitory activity against cell division cycle 25 B phosphatase(Cdc25 B) and protein tyrosine phosphatase 1 B(PTP1 B).The results show that all the compounds 3 display significant inhibitory activities against Cdc25 B,and partial target compounds 3 also show significant inhibitory activities against PTP1 B.Among them,1-(4-nitrobenzoyl)-3-(9-ethyl-carbazole-3-yl)thiourea(3 n) exhibits highest inhibitory activity against Cdc25 B [IC50=(0.49±0.12) ?g/m L] and 1-(2-nitrobenzoyl)-3-(9-ethyl-carbazole-3-yl)thiourea(3 l) displays highest inhibitory activity against PTP1 B [IC50=(3.59±1.15) ?g/m L].It is noteworthy that compound 3 n shows higher inhibitory activity against Cdc25 B and PTP1 B.The preliminary research results of molecular docking revealed the structural-activity of the inhibitors.The active compounds can be considered as potential Cdc25 B and PTP1 B inhibitors,and have great application prospects in the treatment of cancers and diabetes.
引文
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