Microwave assisted synthesis of coumarin-purine derivatives: An approach to in vitro anti-oxidant, DNA cleavage, crystal structure, DFT studies and Hirshfeld surface analysis

Abstract

An easy and efficient microwave-assisted protocol has been developed for the synthesis of coumarin-purine hybrids (3a-3j). The newly constructed 1,3-dimethyl-7-((substituted)-2-oxo-2H-chromen-4-yl)methyl)-1H-purine-2,6(3H,7H)-dione derivatives were evaluated for their in vitro antioxidant activity by DPPH free radical-scavenging ability assay and DNA cleavage by using calf thymus. The compound 3i, shows the most excellent DPPH scavenging activity with a –OH substitution at C7 of coumarin ring. In addition, the structure of compound 3f, has been elucidated using single crystal X-ray diffraction technique. Theoretical calculations (DFT) were carried out using Gaussian09 program package and B3LYP correlation function. Full geometry optimization were carried out using 6-311G++(d, p) basis set and the frontier orbital energy were presented. Hirshfeld surface analysis was used for the intermolecular interactions in the crystal structure. The experimental result of the compound 3f has been compared with the theoretical results and it was found that the experimental data are in a good agreement with the calculated values.

Microwave-Assisted Synthesis of Heterocyclic Scaffolds

“…The microwave-assisted method provides an outstanding yield (up to 97 %) within 5-9 min. 52 S. Kumar et al…”

“…The microwave-assisted method provides an outstanding yield (up to 97 %) within 5–9 min. 52 Gu et al synthesized a variety of indolo[2,3- c ]coumarins 89 (Scheme 21 ) in high yields (up to 93%) through the palladium-catalyzed base-free intramolecular cross-dehydrogenative coupling of quinolinones and 3-amino coumarins under microwave irradiation. 53…”

A Concise Review of Multicomponent Reactions Using Novel Heterogeneous Catalysts under Microwave Irradiation

“…The MI has tremendous applications in various chemistry research areas such as, heterogeneous catalytic reactions [46], solid state chemistry [47], different heterocyclic organic synthesis involving O, N, and S [48], nitrogen containing heterocycles [49], heterocyclic synthetic reactions [50], solvent free heterocyclic synthesis processes [51], colloidal inorganic nanocrystal synthesis [52], bioactive six membered heterocycles synthesis [53], five membered nitrogen heterocycles synthesis [54], Knoevenagel condensation [55], indoles synthesis [56], triazoloquinazolinones and benzimidazoquinazolinones synthesis [57], extraction of volatile compounds [58], oxazoles and diastereoselective oxazolines [59], synthesis of quinazolines and quinazolinones [60], polymer synthesis [61], ferrocenyl chalcone synthesis [62], arylidene acetophenones synthesis [63], photo oxidation of sulfoxides [64], potential biological compounds [65], organic nanoparticle synthesis [66], synthesis of amino-quinazoline derivatives [67], coumarin-purine derivatives [68], various ring opening polymerisation reactions [69], nucleoside protide analogues synthesis [70], organic trans-formations and synthesis [71], benzannulation reactions [72], heterocyclic phosphonate synthesis [73], azha heterocycle synthesis [74], one pot three component pyrazole synthesis [75], heterocyclic hydrazone synthesis [73], degradation reactions [76], heterogeneous catalysis [77,78], 1,2,3 triazolobenzodiazepinones synthesis [79], silica material synthesis…”

Magnetic Surface Molecularly Imprinted Polymer for Selective Adsorption of 4-Hydroxycoumarin

“…Coumarin, as a special natural product, are highly desirable for the widespread applications in biomedical systems and chemistry field due to the prominent pharmacological activities, such as anti-cancer ( Zhao et al, 2019 ), antibacterial ( Elias et al, 2019 ), anti-inflammatory ( Yang et al, 2019 ), antioxidant ( Mangasuli et al, 2019 ) etc. Coumarin is usually an endolipid compound with benzopyranone skeleton.…”