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Synthesis of novel 3-substituted-5H-benzo[5,6][1, 4]thiazino[3,2-e][1,2,4]triazines and their 15-lipoxygenase inhibitory activity

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Abstract

A new group of 3-substituted-5H-benzo[5,6][1,4]thiazino[3,2-e][1,2,4]triazines was designed, synthesized and evaluated as inhibitors of 15-lipoxygenase (15-LO), and the results were compared with those of standard ligand 4-methyl-2-(4-methylpiperazin-1-yl)pyrimido[4,5-b][1,4]benzothiazine (4-MMPB). Among the newly designed ligands, compound 9e showed the best IC50 of 15-LO inhibition (IC50 = 38 µM). The docking calculations were performed in MOE software based on the function of force-field scoring, in order to study the interaction of these new compounds and standard ligand with 15-LO. The docking study implied that these ligands have hydrogen bond interaction with the residue of active site of 15-LO.

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Acknowledgments

We are grateful to Ferdowsi University of Mashhad, Iran, for financial support of this project.

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Authors and Affiliations

  1. Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad, 91775-1436, Iran

    Ali Mohammadi, Hossein Eshghi, Mehdi Bakavoli & Hassanali Moradi

  2. Biotechnology Research Center, School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran

    Farzin Hadizadeh

Authors
  1. Ali Mohammadi
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  2. Hossein Eshghi
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  3. Mehdi Bakavoli
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  4. Farzin Hadizadeh
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  5. Hassanali Moradi
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Correspondence to Mehdi Bakavoli or Farzin Hadizadeh.

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Dedicated to the memory of Professor Mohammad Rahimizadeh.

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Mohammadi, A., Eshghi, H., Bakavoli, M. et al. Synthesis of novel 3-substituted-5H-benzo[5,6][1, 4]thiazino[3,2-e][1,2,4]triazines and their 15-lipoxygenase inhibitory activity. J IRAN CHEM SOC 13, 1539–1547 (2016). https://doi.org/10.1007/s13738-016-0870-6

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