Synthesis and SAR studies of 3-allyl-4-prenyloxyaniline amides as potent 15-lipoxygenase inhibitors

Jabbari, Atena; Davoodnejad, Mahdieh; Alimardani, Maliheh; Assadieskandar, Amir; Sadeghian, Ali; Safdari, Hadi; Movaffagh, Jebrail; Sadeghian, Hamid

doi:10.1016/j.bmc.2012.07.025

Cited by 16 publications

(13 citation statements)

References 28 publications

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“…The lipo‐oxygenase inhibitory potency of all of the mono‐hydroxycoumarins was studied against human 15‐LOX‐1 using the modified oxidative coupling of 3‐methyl‐2‐benzothiazolinone (MBTH) with 3‐(dimethylamino) benzoic acid (DMAB), which was reported by Jabbari et al . Human 15‐LOX‐1 was prepared from isolated human eosinophil based on the procedure reported by Jabbari et al …”

Section: Resultsmentioning

confidence: 99%

A novel class of human 15‐LOX‐1 inhibitors based on 3‐hydroxycoumarin

et al. 2018

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Inflammations, sensitivities, and some cancers in mammals are intimately linked to the activity of lipo-oxygenase enzymes. Owing to the importance of these enzymes, mechanistic studies, product analysis, and synthesis of inhibitors have expanded. In this study, a series of hydroxycoumarins, methoxy-3-hydroxy coumarins, and 7-alkoxy-3-hydroxy coumarins were synthesized and evaluated as potential inhibitors of human 15-LOX-1. Among the synthetic coumarins, 7-methoxy-3-hydroxycoumarin derivative demonstrated potent inhibitory activity and the compound, 5f, showed the best result. Radical scavenging assessment, IC , HNMR, and DPPH bleaching results indicate that the electronic properties are the major factors for the lipo-oxygenase inhibition potency of the synthetic coumarins. Based on the theoretical studies, it was suggested that the mesomeric effect of the substituent at the seventh position of the benzene ring is one of the major factors in the stability of the oxy-radical intermediate.

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Section: Resultsmentioning

confidence: 99%

A novel class of human 15‐LOX‐1 inhibitors based on 3‐hydroxycoumarin

et al. 2018

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“…The inhibitory property of compounds 6a-g on 15-LO was assessed according to our previously reported procedure [1,7]. The compounds show low inhibitory activity.…”

Section: Resultsmentioning

confidence: 99%

“…SLO inhibitory assessment was performed by the Research Biochemistry Laboratory (Department of Laboratory Sciences, Mashhad University of Medical Science) using the previously published procedure [7].…”

Section: -Lo Inhibitory Assessmentmentioning

confidence: 99%

Synthesis of new derivatives of 10H-benzo[b]pyridazino[3,4-e][1,4]thiazines

Arghiani

Seyedi

Bakavoli

et al. 2015

Heterocyclic Communications

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“…17 The efficiency of this method to produce bonding models similar to the experimentally results has been reported. 18,19 The docking regions of 1BLC and 1K6S were defined with the considering Cartesian chart 4.08, À8.312, À12.31 and 5.53, 13.81, 64.95 as the center of a grid with 52, 44, 63 and 50, 50, 50 points in X, Y and Z axes, respectively. The docking parameter files were generated using Genetic Algorithm and Local Search Parameters while the number of generations (Genetic Algorithm and Local Search Parameters runs) and the maximum number of energy evaluations was set to 200 and 2,500,000, respectively (number of individuals in the population ¼ 300).…”

Section: Materials and Methods Molecular Modeling Docking And Sar Studymentioning

confidence: 99%

Potent and selective inhibitors of class A β-lactamase: 7-prenyloxy coumarins

et al. 2014

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Class A and D β-lactamases are the main causes of resistance against β-lactam antibiotics, especially the penam group, in Staphylococcus aureus. On the basis of the potentiator property of ethanolic extracts of Ferula szowitsiana root on penicillin, MIC values observed for resistant S. aureus, the main naturally occurring compounds in these extracts, auraptene, umbelliprenin and galbanic acid, were evaluated for β-lactamase inhibitory activity. Amongst them auraptene showed the most potent inhibitory activity (IC50=21±1.5 μM) toward class A β-lactamase, whereas no inhibition was observed for class D β-lactamase. To obtain the structure activity relationship of the mentioned compounds and rationalize the enzyme inhibitory results, docking analysis was performed for both groups of β-lactamases. Docking analysis showed that the compounds have 100-500-fold lower bonding affinity toward the class D β-lactamase than toward the class A enzyme.

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Synthesis and SAR studies of 3-allyl-4-prenyloxyaniline amides as potent 15-lipoxygenase inhibitors

Cited by 16 publications

References 28 publications

A novel class of human 15‐LOX‐1 inhibitors based on 3‐hydroxycoumarin

A novel class of human 15‐LOX‐1 inhibitors based on 3‐hydroxycoumarin

Synthesis of new derivatives of 10H-benzo[b]pyridazino[3,4-e][1,4]thiazines

Potent and selective inhibitors of class A β-lactamase: 7-prenyloxy coumarins

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