Author:
Abbas Saghir,Zaib Sumera,Ali Saqib,Iqbal Jamshed
Abstract
Objective: The synthesis, characterization, 15-LOX inhibition and molecular docking studies of a commercially available NSAID, flurbiprofen and its derivatives. Study Design: Experimental study. Place and Duration of Study: The study was carried out at Quaid-i-Azam University and Centre for Advanced Drug Research COMSATS University Islamabad, Abottabad Campus from March 2019 to February 2020. Materials and Methods: The structural elucidation of the compounds (2-5) was carried out using infrared, 1H and 13C NMR spectroscopic studies. The structure of 4-amino-5-(1-(2-fluorobiphenyl-4-yl)-ethyl)-4H-1,2,4- triazole-3-thione (5) was also verified by single crystal X-ray diffraction (XRD) studies. Results: The most potent inhibitor for 15-LOX (2) has an IC50value of0.18 ± 0.01 μM. Molecular docking results of 1, 2, 3 and cognate ligand inside the active site of 15-LOX (PDB ID: 1IK3) revealed significant correlation. Conclusion: This work represents cost-effective, reproducible and facile conversion of an aromatic monocarboxylic acid into potent derivatives.The molecules 2-(2-fluorobiphenyl-4-yl) propanoic acid (1) and its derivatives (2-5) possess 15-LOX inhibition and can be a prospective therapeutic target for chronic obstructive pulmonary disease.
Publisher
National University of Medical Sciences
Cited by
6 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献
1. Molecular hybrids of substituted phenylcarbamoylpiperidine and 1,2,4-triazole methylacetamide as potent 15-LOX inhibitors: Design, synthesis, DFT calculations and molecular docking studies;Bioorganic Chemistry;2024-02
2. Synthesis and characterization of biologically active flurbiprofen amide derivatives as selective prostaglandin-endoperoxide synthase II inhibitors: In vivo anti-inflammatory activity and molecular docking;International Journal of Biological Macromolecules;2023-02
3. Vetting of new N-furfurylated p-chlorophenyl-1,2,4-triazole acetamides as lipoxygenase inhibitors assisted with in vitro and in silico studies;Journal of the Iranian Chemical Society;2023-01-04
4. Identification of novel diclofenac acid and naproxen bearing hydrazones as 15-LOX inhibitors: Design, synthesis, in vitro evaluation, cytotoxicity, and in silico studies;Arabian Journal of Chemistry;2022-12
5. Synthetic Transformation of 2-{2-Fluoro[1,1′-biphenyl]-4-yl} Propanoic Acid into Hydrazide–Hydrazone Derivatives: In Vitro Urease Inhibition and In Silico Study;ACS Omega;2022-11-30