Synthesis, antioxidant, and xanthine oxidase inhibitory activities of 5-[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione derivatives.

Xanthine oxidase (XO) is a complex metalloflavoprotein, the overproduction of which usually leads to a pathological condition called gout. The XO inhibitors may prove to be promising antigout agents. The XO generates superoxide anions and H2O2 for the self-defense system of the organism. Abnormal production of this superoxide (reactive oxygen species) is responsible for a number of complications including inflammation, metabolic disorder, cellular aging, reperfusion damage, atherosclerosis, and carcinogenesis. In this paper, we report the synthesis of N-substituted analogs of thiazolidinedione derivatives as effective and new class of XO inhibitors and also as antioxidant agents. Among all the compounds in the series, compound 2i produced relatively better activity against human milk XO (72% inhibition), which was also supported by docking studies.

Synthesis, xanthine oxidase inhibition, and antioxidant screening of benzophenone tagged thiazolidinone analogs.

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.

2-Benzoyl-4-chloro-phenyl benzoate.

In the title compound, C20H13ClO3, the dihedral angles between the benzoate and the chloro-benzene and benzoyl rings are 68.82 (5) and 53.76 (6)°, respectively, while the dihedral angle between the benzoyl and benzoate rings is 81.17 (5)°. The eight atoms of the benzoyl residue are essentially planar with the exception of the O atom which lies 0.1860 (5) Šout of their mean plane (r.m.s. deviation = 0.97 Å). The nine atoms of benzoate residue are also essentially planar (r.m.s. deviation = 0.20 Å) with the ester O atom showing the greatest deviation [0.407 (12) Å] from their mean plane. In the crystal, mol-ecules are connected into centrosymmetric dimers by pairs of C-H⋯O hydrogen bonds.