In Vitro Antioxidant Activity of Selected 4-Hydroxy-chromene-2-one Derivatives—SAR, QSAR and DFT Studies

Abstract

The series of fifteen synthesized 4-hydroxycoumarin derivatives was subjected to antioxidant activity evaluation in vitro, through total antioxidant capacity, 1,1-diphenyl-2-picryl-hydrazyl (DPPH), hydroxyl radical, lipid peroxide scavenging and chelating activity. The highest activity was detected during the radicals scavenging, with 2b, 6b, 2c, and 4c noticed as the most active. The antioxidant activity was further quantified by the quantitative structure-activity relationships (QSAR) studies. For this purpose, the structures were optimized using Paramethric Method 6 (PM6) semi-empirical and Density Functional Theory (DFT) B3LYP methods. Bond dissociation enthalpies of coumarin 4-OH, Natural Bond Orbital (NBO) gained hybridization of the oxygen, acidity of the hydrogen atom and various molecular descriptors obtained, were correlated with biological activity, after which we designed 20 new antioxidant structures, using the most favorable structural motifs, with much improved predicted activity in vitro.

Crystal structure of 1,4-dihydro-1-phenylchromeno[4,3-c]pyrazole, C16H12N2O

“…On the other hand, chromene derivatives play important roles in biological and pharmacological activities such as antivascular, antitumor, antibacterial, antiin ammatory, and antimicrobial activities [2][3][4]. In our previous work, we report the synthesis and pharmacological activities of some other nitrogen-based heterocyclic derivatives as analgesic and anti-in ammatory [5][6][7], SARS-CoV 3C-like protease inhibitors [8], monoamino oxidase inhibitors [9], anticancer [10,11], and antimicrobial [12] agents.…”

Microwave‐assisted rapid and efficient synthesis of chromene‐fused pyrrole derivatives through multicomponent reaction and evaluation of antibacterial activity with molecular docking investigation

“…Plenty of chromene derivatives are present in nature, and it exhibited broad therapeutic activity including antibacterial activity 7, [22][23][24] anticancer activity 8, [25] antiviral activity, [26] anticonvulsant activity, [27] antiproliferative activity 9, [28] antitubercular, [29] antioxidant, [30] antifungal, [31] and TNF-α inhibitory activities [32] (Figure 1). Plenty of chromene derivatives are present in nature, and it exhibited broad therapeutic activity including antibacterial activity 7, [22][23][24] anticancer activity 8, [25] antiviral activity, [26] anticonvulsant activity, [27] antiproliferative activity 9, [28] antitubercular, [29] antioxidant, [30] antifungal, [31] and TNF-α inhibitory activities [32] (Figure 1).…”

Synthesis of New Imino Containing Tetrahydrochromeno[2,3‐d]pyrimidines

“…The chromene moiety appears as an important structural component in both biologically active and natural compounds and is widely employed as cosmetics, pigments , and potential biodegradable agrochemicals . It is known that certain chromenes possess important biological activities such as antioxidant , anticancer , anti‐HIV , antiviral , antihypertensive , anticonvulsant , antileishmanial , TNF‐α inhibitor , and antifungal activity. This motif widely found in natural alkaloids, tocopherols, flavonoids, and anthocyanins , and several chromene derivatives have been proven to be efficient DNA polymerase β inhibitors and apoptosis inducers .…”