Microwave-Assisted Synthesis, Characterization, Docking Studies and Molecular Dynamic of Some Novel Phenyl Thiazole Analogs as Xanthine Oxidase Inhibitor

• Published in: Journal of the Iranian Chemical Society Vol. 19; no. 9; pp. 3919 - 3933
• Main Authors: Jyothi, Mahima, Khamees, Hussien Ahmed, Patil, Shashank M., Ramu, Ramith, Khanum, Shaukath Ara
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01-09-2022; Springer Nature B.V
• Subjects: Acetophenone; Analytical Chemistry; Biochemistry; Bromination; Chemical synthesis; Chemistry; Chemistry and Materials Science; Inorganic Chemistry; Mass spectra; Molecular docking; Molecular dynamics; NMR; Nuclear magnetic resonance; Organic Chemistry; Original Paper; Physical Chemistry; Substitutes; Xanthine oxidase; Docking study; Phenyl thiazole microwave synthesis; Xanthine oxidase inhibition
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-022-02574-z

A series of novel substituted 2-(4-bromophenyl)-4-phenylthiazole compounds
5a–h
were synthesized by a simplified two-step process. First, the selective and effective α-bromination of substituted acetophenone moieties with N-bromo succinamide was done followed by treating of substituted 2-bromo-1-phenylethan-1-one with 4-bromobenzothiamide under microwave irradiation. The structures of the newly synthesized compounds were confirmed by IR,
1
H NMR,
13
C NMR, mass spectra and C, H, N analysis. Further, all the synthesized compounds
5a–h
were evaluated for xanthine oxidase inhibition. Among all the tested compounds,
5f
was found to be highly potent (IC
50
 = 0.100 ± 0.08 µM) followed by
5e
(IC
50
 = 0.145 ± 1.42 µM), compared to the standard allopurinol (IC
50
 = 0.150 ± 0.07 µM), which is evident from in vitro and in silico analysis.