Design, synthesis, molecular docking study and biological evaluation of heteroaryl 2-phenoxypyridin-3-yl derivatives as lipoxygenase enzyme inhibitors

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Najjari Zeinab; Mirjalili Johreh; NADRI HAMID; Rabbani Faezeh; MORADI ALIREZA

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Journal: Journal of Shahid Sadoughi University of Medical Sciences Year:2018 | Volume:26 | Issue:7 Page(s): 583-598

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Information Journal Paper

Title

Design, synthesis, molecular docking study and biological evaluation of heteroaryl 2-phenoxypyridin-3-yl derivatives as lipoxygenase enzyme inhibitors

Author(s)

Keywords

Lipoxygenase InhibitorsQ1

Molecular Docking SimulationQ1

2Q1

phenoxypyridineQ1

3Q1

yl DerivativesQ1

Abstract

Introdution: Lipoxygenase enzyme is responsible for biosynthesis of leukotrienes that possess various pharmacological effects in the body. The beneficial therapeutic effects of Lipoxygenase Inhibitors have been proved in some diseases such as asthma, cancer and Alzheimer’ s disease. So, the Lipoxygenase Inhibitors could be used in the treatment of some diseases and pathological conditions. In this study, heteroaryl 2-phenoxypyridine-3-yl Derivatives have been synthesized and evaluated as Lipoxygenase Inhibitors. Methods: In this basic-applied study, the desired derivatives were synthesized in multiple steps using convenient methods. Then, the structure of compounds was validated using infrared, mass and nuclear magnetic resonance spectroscopy. Finally, lipoxygenase inhibitory activity of compounds was evaluated and molecular docking studies was performed on the most active compound. Results: All target compounds were synthesized in good yields and showed good inhibitory activity against lipoxygenase (IC50 =100-179  M) in comparison to Quercetin (IC50 = 58. 5  M) as standard inhibitor. The compound 7a (5-(2-phenoxypyridine-3-yl)-1, 3, 4-oxadiazole-2(3H)-thione) showed the most potent activity and the molecular docking studies showed that this compound was well fitted in the active site of enzyme. Conclusion: The synthesized compounds have shown good inhibitory activity against lipoxygenase and the molecular docking studies show that these compounds are able to fit in the active site of enzyme. Therefore, the target compounds could be used as lead compounds for further studies to find novel lipoxygenase inhibitor drugs.

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APA: Copy

Najjari, Zeinab, Mirjalili, Johreh, NADRI, HAMID, Rabbani, Faezeh, & MORADI, ALIREZA. (2018). Design, synthesis, molecular docking study and biological evaluation of heteroaryl 2-phenoxypyridin-3-yl derivatives as lipoxygenase enzyme inhibitors. JOURNAL OF SHAHID SADOUGHI UNIVERSITY OF MEDICAL SCIENCES, 26(7 ), 583-598. SID. https://sid.ir/paper/35700/en

Vancouver: Copy

Najjari Zeinab, Mirjalili Johreh, NADRI HAMID, Rabbani Faezeh, MORADI ALIREZA. Design, synthesis, molecular docking study and biological evaluation of heteroaryl 2-phenoxypyridin-3-yl derivatives as lipoxygenase enzyme inhibitors. JOURNAL OF SHAHID SADOUGHI UNIVERSITY OF MEDICAL SCIENCES[Internet]. 2018;26(7 ):583-598. Available from: https://sid.ir/paper/35700/en

IEEE: Copy

Zeinab Najjari, Johreh Mirjalili, HAMID NADRI, Faezeh Rabbani, and ALIREZA MORADI, “Design, synthesis, molecular docking study and biological evaluation of heteroaryl 2-phenoxypyridin-3-yl derivatives as lipoxygenase enzyme inhibitors,” JOURNAL OF SHAHID SADOUGHI UNIVERSITY OF MEDICAL SCIENCES, vol. 26, no. 7 , pp. 583–598, 2018, [Online]. Available: https://sid.ir/paper/35700/en

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