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Synthesis, biological evaluation and molecular docking of 3-substituted quinazoline-2,4(1 H , 3 H )-diones
Journal of Chemical Sciences ( IF 1.7 ) Pub Date : 2020-08-08 , DOI: 10.1007/s12039-020-01813-1 Lumadhar Santos-Ballardo , Fernando García-Páez , Lorenzo A Picos-Corrales , Adrián Ochoa-Terán , Pedro Bastidas , Loranda Calderón-Zamora , Guadalupe Rendón-Maldonado , Ulises Osuna-Martínez , Juan I Sarmiento-Sánchez
中文翻译:
3-取代的喹唑啉-2,4(1 H,3 H)-二酮的合成,生物学评价和分子对接
更新日期:2020-08-08
Journal of Chemical Sciences ( IF 1.7 ) Pub Date : 2020-08-08 , DOI: 10.1007/s12039-020-01813-1 Lumadhar Santos-Ballardo , Fernando García-Páez , Lorenzo A Picos-Corrales , Adrián Ochoa-Terán , Pedro Bastidas , Loranda Calderón-Zamora , Guadalupe Rendón-Maldonado , Ulises Osuna-Martínez , Juan I Sarmiento-Sánchez
Abstract
The quinazoline-2,4-diones scaffold is found in bioactive compounds, commercial drugs and exhibit important biological activities. However, their antidiabetic activity is rarely explored. For this purpose, an easy one-pot three-components and straightforward synthesis of 3-substituted quinazoline-2,4-diones was designed, in both, the catalyst- and solvent-free conditions under microwave irradiation. Additionally, the synthesized compounds were screened for in vitro α-amylase and α-glucosidase inhibitory activity, as well as antioxidants and cytotoxicity. The quinazoline-2,4-diones were isolated, with yields in the range of 30-65%. The compounds 3d, 3e, 3g and 3h displayed moderate activity against α-amylase and/or α-glucosidase enzymes compared with the acarbose drug. The molecular docking study revealed that all active compounds displayed a different type of intermolecular interaction in the pocked site of these enzymes. Interestingly, in the Artemia salina assay, the compound 3d exhibited a higher cytotoxic effect than 5-fluorouracil. All these results support the pharmacological potential of quinazoline-2,4-diones since all evaluated compounds behave as moderate inhibitors of the enzymes α-amylase and/or α-glucosidase.Graphic abstract
An easy one-pot three-components and straightforward synthesis of 3-substituted quinazoline-2,4-diones was designed, in both, the catalyst- and solvent-free conditions under microwave irradiation. Moreover, the in vitro α-amylase and α-glucosidase inhibitory activity, as well as antioxidants and cytotoxicity are reported.中文翻译:
3-取代的喹唑啉-2,4(1 H,3 H)-二酮的合成,生物学评价和分子对接