5943-92-0Relevant articles and documents
Catalytic formation of N3-substituted quinazoline-2,4(1: H,3 H)-diones by Pd(ii)EN?GO composite and its mechanistic investigations through DFT calculations
Biswas, Surajit,Dolai, Malay,Haque Biswas, Imdadul,Haque, Najirul,Islam, Md Sarikul,Islam, Sk Manirul,Khatun, Resmin,Sengupta, Manideepa
, p. 141 - 151 (2020)
In the current era, the scientific community is very much interested to utilize the greenhouse gas, carbon dioxide, through chemical fixation in order to produce value-based fine organic chemicals. The chemical combination of atmospheric carbon dioxide, isocyanides, and 2-iodoaniline in a one-pot reaction for the synthesis of quinazoline-2,4(1H,3H)-dione derivatives is a straight forward and attractive methodology to avoid multi-step and more toxic reagent containing routes. In this study, a heterogeneous catalyst was designed and synthesized from aminically modified graphene oxide by the incorporation of palladium metal. The catalyst was characterized by FT-IR, XRD, ICP-AES, Raman spectroscopy, XPS, TEM, SEM, EDX, and N2 absorption desorption studies. In this report, the formation of N3-substituted 2,4(1H,3H)-quinazolinediones was performed under mild and heterogeneous reaction conditions under 1 bar CO2 pressure. The catalyst is very efficient to produce the quinazoline derivatives. For the investigation of the mechanistic route of the catalytic reaction, density functional theory (DFT) calculations were also monitored. We have checked the recyclability of the catalyst, the results indicated that the catalyst maintained its catalytic efficacy even after six cycles of use.
Synthesis, biological evaluation and molecular docking of 3-substituted quinazoline-2,4(1H, 3H)-diones
Bastidas, Pedro,Calderón-Zamora, Loranda,García-Páez, Fernando,Ochoa-Terán, Adrián,Osuna-Martínez, Ulises,Picos-Corrales, Lorenzo A,Rendón-Maldonado, Guadalupe,Santos-Ballardo, Lumadhar,Sarmiento-Sánchez, Juan I
, (2020/08/14)
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 30-65percent. 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.[Figure not available: see fulltext.]
Green synthesis of quinazolinone derivatives catalyzed by iodine in ionic liquid
Wang, Shu-Liang,Yang, Ke,Yao, Chang-Sheng,Wang, Xiang-Shan.
experimental part, p. 341 - 349 (2011/11/12)
A series of quinazolinone derivatives were synthesized by the reaction of 2-aminobenzamides and triethyl orthoformate or triphosgene in ionic liquid of [BMIm]BF4 at 80 °C catalyzed by iodine in good yields. Compared to other methods, this new procedure has the advantages of mild reaction conditions, good yields, operational simplicity, and environmentally friendly procedure. Copyright Taylor & Francis Group, LLC.
