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

Alavi, Seyed Jamal; Sadeghian, Hamid; Seyedi, Seyed Mohammad; Salimi, Alireza

doi:10.1111/cbdd.13174

Cited by 10 publications

(7 citation statements)

References 22 publications

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“…The desired allyl and diallyl phenols were synthesized by Claisen rearrangement on the related allyoxyphenols. After preparation and full characterization of the monoallyl compounds, The LOX inhibitory potency was studied against 15‐hLOX‐1 using the modified oxidative coupling of 3‐methyl‐2‐benzothiazolinone (MBTH) with 3‐(dimethylamino) benzoic acid (DMAB), which was reported by Alavi et al (Alavi et al, 2018). After investigating the enzyme inhibition results of the monoallyl compounds, the best inhibitors were selected for converting to diallyl analogs.…”

Section: Resultsmentioning

confidence: 99%

“…The immediate products of fatty acid oxidation by LOX have been shown to be associated with acute and chronic diseases such as stroke, myocardial infarction, asthma, cancer, inflammation and many other diseases and pathological states. Due to the importance of LOX as therapeutic target, there is currently much interest for the discovery and synthesis of novel and potent LOX inhibitors (Alavi, Sadeghian, Seyedi, Salimi, & Eshghi, 2018; Mousavian et al, 2020; Sadeghian, Seyedi, Saberi, Arghiania, & Riazi, 2008).…”

Section: Introductionmentioning

confidence: 99%

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Allylphenols as a new class of human 15‐lipoxygenase‐1 inhibitors

Alavi

Seyedi

Saberi

et al. 2020

Drug Development Research

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In this study, a series of mono‐ and diallylphenol derivative were designed, synthesized, and evaluated as potential human 15‐lipoxygenase‐1 (15‐hLOX‐1) inhibitors. Radical scavenging potency of the synthetic allylphenol derivatives was assessed and the results were in accordance with lipoxygenase (LOX) inhibition potency. It was found that the electronic natures of allyl moiety and para substituents play the main role in radical scavenging activity and subsequently LOX inhibition potency of the synthetic inhibitors. Among the synthetic compounds, 2,6‐diallyl‐4‐(hexyloxy)phenol (42) and 2,6‐diallyl‐4‐aminophenol (47) showed the best results for LOX inhibition (IC50 = 0.88 and 0.80 μM, respectively).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Allylphenols as a new class of human 15‐lipoxygenase‐1 inhibitors

Alavi

Seyedi

Saberi

et al. 2020

Drug Development Research

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“…Because of their importance as therapeutic targets, work has been devoted to the discovery of pathways for the synthesis of new and potent inhibitors of this lipo-oxygenase. Several natural and synthetic derivatives of hydroxycoumarins have been reported as lipo-oxygenase inhibitors [63][64][65][66][67]. Most of them inhibit lipo-oxygenase pathways using the redox mechanism with their hydroxyl groups.…”

Section: Human 15-lox-1 Inhibitors Based On 3-hydroxycoumarinmentioning

confidence: 99%

“…Most of them inhibit lipo-oxygenase pathways using the redox mechanism with their hydroxyl groups. Alavi et al [66] analysed the lipo-oxygenase inhibitory power of monohydroxycoumarins against human 15-LOX-1 enzymes and their radical scavenging activity was comparatively observed. Among the coumarins mentioned, the 3-hydroxy derivative was the potent lipo-oxygenase inhibitor with an IC50 value of 9.5 µm.…”

Section: Human 15-lox-1 Inhibitors Based On 3-hydroxycoumarinmentioning

confidence: 99%

Overview of Recent Advances in 3-Hydroxycoumarin Chemistry as a Bioactive Heterocyclic Compound

Yoda¹

2020

AJHC

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Coumarins or benzo-2-pyrone derivatives are one of the most significant families of natural compounds and are also important in synthetic organic chemistry. They have been widely used as starting materials or precursor molecules in the pharmaceutical, perfumery and agrochemical industries, etc. Hydroxycoumarins are an important class of coumarin compounds that possess several physical, chemical and biological properties. Among the hydroxycoumarins, 3-hydroxycoumarin seems to be the most important because of its numerous chemical, photochemical and biological properties. However, this compound remains less well known compared to others of the same class such as 7-hydroxycoumarin and 4-hydroxycoumarin. This study is therefore devoted to 3-hydroxycoumarin and its applications. The main purpose of this review is to summarize and document the recent advances on 3-hydroxycoumarin, concerning the main routes of its synthesis, its reactivity, its applications in different fields of biology. Several methods for the synthesis of 3-hydroxycoumarin have been described in the literature, most of which use salicylic aldehyde and 1-(2-hydroxyphenyl)ethanone as starting compounds. Other synthesis pathways exist, but they are based on intermediate synthesis compounds. Concerning the reactivity of 3-hydroxycoumarin, many heterocyclic compounds obtained from 3-hydroxycoumarin have been reported in the literature. Among these heterocycles are pyrido[2,3-c]coumarin derivatives, chromeno[4,3-e][1,3]oxazine derivatives, dihydropyrano[2,3-c] chromenes and 3-coumarinyl carboxylates. Various researches have also concerned the biological properties of this compound. It appears from these numerous studies that 3-hdroxycoumarin is used in fields such as genetics, pharmacology, microbiology, etc.

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“…Several natural and synthetic derivatives of hydroxycoumarins have been reported as inhibitors of the lipoxygenase pathways (Alavi et al, 2018; Kontogiorgis & Hadjipavlou‐Litina, 2005). Most of them inhibit the lipoxygenase activity using redox mechanism via their hydroxyl groups.…”

Section: Introductionmentioning

confidence: 99%

O‐prenylated carbostyrils as a novel class of 15‐lipoxygenase inhibitors: Synthesis, characterization, and inhibitory assessment

et al. 2021

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Catalyzed peroxidation of unsaturated lipid in animals and plants intimately is linked to the activity of 15-Lipoxygenase enzymes. Lipoxygenases (LOXs) are well known to play an important role in many acute and chronic syndromes such as inflammation, asthma, cancer, and allergy. In this study, a series of mono prenyloxycarbostyrils were synthesized and evaluated as potential inhibitors of soybean 15-Lipoxygenase (SLO) and their inhibitory potencies were compared to mono prenyloxycoumarins which had been reported in the previous works.The synthetic compounds inhibit lipoxygenase enzyme by competitive mechanism like the prenyloxy coumarins. The results showed that position and length of the prenyl moiety play the important role in lipoxygenase inhibitory activity. Among all of the synthetic compounds (coumarin and carbostyril derivatives), 5-farnesyloxycoumarin and 8-farnesyloxycarbostyril demonstrated the best inhibitory activity by IC 50 values of 1.1 µM and 0.53 µM, respectively.

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

Cited by 10 publications

References 22 publications

Allylphenols as a new class of human 15‐lipoxygenase‐1 inhibitors

Allylphenols as a new class of human 15‐lipoxygenase‐1 inhibitors

Overview of Recent Advances in 3-Hydroxycoumarin Chemistry as a Bioactive Heterocyclic Compound

O‐prenylated carbostyrils as a novel class of 15‐lipoxygenase inhibitors: Synthesis, characterization, and inhibitory assessment

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