Synthesis, Xanthine Oxidase Inhibition, and Antioxidant Screening of Benzophenone Tagged Thiazolidinone Analogs

Abstract

A series of novel 2-(diaryl methanone)-N-(4-oxo-2-phenyl-thiazolidin-3-yl)-acetamides were synthesized by various Schiff bases of (4-benzoyl-phenoxy)-aceto hydrazide with thioglycolic acid. The structures of the newly synthesized compounds were confirmed by IR, (1) H NMR, mass spectra, and C, H, N analysis. Further, all the synthesized compounds 9a-n were evaluated for xanthine oxidase (XO) inhibition and antioxidant properties. Among all the tested compounds, 9f, 9m, and 9n demonstrated potent XO inhibition of 52, 76, and 26%, respectively, compared to the standard drug allopurinol, which is evident from in vitro and in silico analysis. On the other hand, compounds 9c, 9d, and 9k exhibit potent antioxidant properties.

Anti-Hyperuricemic Effect of 2-Hydroxy-4-methoxy-benzophenone-5-sulfonic Acid in Hyperuricemic Mice through XOD

“…Many synthesized compounds or natural products against it were developed or discovered, taking compounds with the core scaffolds of six-membered ring, with bicyclic structure, tricyclic structure and condensed tetracyclic structures as examples [ 28 ]. As a typical bicyclic structure, benzophenones with hydroxyls [ 22 ] or thiazolidinone groups [ 23 ] were synthesized and found to be active against XOD. Specially, the most active one, 2,2′,4,4′-tetrahydroxybenzophenone, exhibited a IC 50 of 47.59 μM [ 22 ] and compound 9m displayed about 76% of the activity of allopurinol [ 23 ].…”

“…As a typical bicyclic structure, benzophenones with hydroxyls [ 22 ] or thiazolidinone groups [ 23 ] were synthesized and found to be active against XOD. Specially, the most active one, 2,2′,4,4′-tetrahydroxybenzophenone, exhibited a IC 50 of 47.59 μM [ 22 ] and compound 9m displayed about 76% of the activity of allopurinol [ 23 ]. However, it was not clear whether they could reduce SUA in vivo, although they provided a novel skeleton against hyperuricemia.…”

“…Besides, a series of synthesized benzophenones exhibited anti-proliferative activity against DLA cells [ 21 ]. In our studies, some of them exhibited good XOD inhibitory activities, such as those substituted by hydroxyls [ 22 ] and thiazolidinone groups [ 23 ], making them promising as potential anti-hyperuricemic agents, although their in vivo anti-hyperuricemic effects were not reported. Of benzophenone-type chemicals, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid (HMS, Figure 1 ) is the most popular UV-filter, with a maximum permitted concentration in cosmetics currently set at 6% (USA), 5% (EU and China), and 10% (Japan) [ 1 ], which was much higher than doses in drugs (μM in vitro or mg/kg in vivo).…”

An efficient synthesis of designed 4‐thiazolidinone fused pyrimidine derivatives as potent antimicrobial agents

“…On the other hand, numerous thiazolidinones containing various heterocylces have also proven to be of better pharmacological and therapeutically interest. The chemistry of thiazolidinone compounds has received a great interest because of their interesting biological activities such as anticonvulsant, [13] hypnotic, [14] antiinflammatory, [15] anticancer, [16] antioxidant, [17] antiproteolytic, [18] antitubercular, [19] anthelmintic, [20] cardiovascular effects, [21] antibacterial, [22,23] antiviral, [24] antifungal, [25] insecticidal and herbicidal activities. In recent years, part of our research effort has focused on the synthesis and application of thiazolidinone derivatives containing heterocyclic rings.…”

SYNTHESIS AND STUDY OF ANTIOXIDATIVE PROPERTIES OF AMINOMETHYLATED DERIVATIVES OF p-(CYCLOHEXENE3-YL-ETHYLPHENOL)

“…The use of antioxidants is economically advantageous, so their production in technologically advanced countries is ahead of other chemical production [7][8][9][10][11].…”