Design,synthesis and SAR studies of 4-allyoxyaniline amides as potent 15-lipoxygensae inhibitors |
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Authors: | Seyed Mohammad Seyedi Zeinab Jafari Neda Attaran Hamid Sadeghian Mohammad Reza Saberi Mohammad Mahdi Riazi |
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Institution: | 1. Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Mashhad 917751436, Islamic Republic of Iran;2. School of Pharmacy, Pharmaceutical Research Center, Mashhad University of Medical Sciences, BuAli Square, Mashhad 9196773117, Islamic Republic of Iran |
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Abstract: | A group of 4-allyloxyaniline amides 5a–o were designed, synthesized and evaluated as potential inhibitors of soybean 15-lipoxygenase (SLO) on the basis of eugenol and esteragol structures. Compound 5e showed the best IC50 in SLO inhibition (IC50 = 0.67 ± 0.06 μM). All compounds were docked in SLO active site retrieved from RCSB Protein Data Bank (PDB entry: 1IK3) and showed that allyloxy group of compounds is oriented towards the Fe3+-OH moiety in the active site of enzyme and fixed by hydrogen bonding with two conserved His513 and Gln716. It is resulted that molecular volume of the amide moiety would be a major factor in inhibitory potency variation of the synthetic amides, where the hydrogen bonding of the amide group could also involve in the activity of the inhibitors. |
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