Lipoxygenase inhibitors: A comparative QSAR study review and evaluation of new QSARs

Pontiki, Eleni; Hadjipavlou‐Litina, Dimitra

doi:10.1002/med.20099

Cited by 74 publications

(67 citation statements)

References 75 publications

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“…It is important to be noticed that the transformation of a3 to the bis-chalcone ether b3 led to a more potent derivative (IC 50 ¼ 56 lM). Lipophilicity was referred as an important physicochemical property for LOX inhibition 40 . This physicochemical property could explain the increase of anti-LOX activity in b3 (clog P values for a3 ¼ 3.66, whereas b3 ¼ 9.00).…”

Section: Biological Evaluationmentioning

confidence: 99%

“…There is no universally accepted approach to evaluate the relative potency of different substances to cause LOX inhibition. However, most of the LOX inhibitors are antioxidants or free radical scavengers 40 . Herein, the results from the anti-lipid peroxidation activity studies support the anti-LOX activity for the bis-halcones b1-b4.…”

Section: Biological Evaluationmentioning

confidence: 99%

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Simple chalcones and bis-chalcones ethers as possible pleiotropic agents

Liargkova

Hadjipavlou‐Litina

Koukoulitsa

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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The synthesis, the antioxidative properties and the lipoxygenase (LOX) and acetylcholinesterase (AChE) inhibition of a number of 4-hydroxy-chalcones diversely substituted as well as of a series of bis-chalcones ether derivatives are reported. The chalcones derivatives were readily produced using a Claisen-Schmidt condensation in a ultra sound bath in good yields. The structures of the synthesized compounds were confirmed by spectral and elemental analysis. Their lipophilicity is experimentally determined by reversed-phase thin-layer chromatography method. Most of them are potent in vitro inhibitors of lipid peroxidation and of LOX. Compounds b2 and b3 were found to be the most potent LOX and AChE inhibitors among the tested derivatives with a significant anti-lipid peroxidation profile. The results led us to propose these enone derivatives as new multifunctional compounds against Alzheimer's disease. The results are discussed in terms of structural and physicochemical characteristics of the compounds. Moreover, the pharmacokinetic profile of these compounds was investigated using computational methods.

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Section: Biological Evaluationmentioning

confidence: 99%

Section: Biological Evaluationmentioning

confidence: 99%

Simple chalcones and bis-chalcones ethers as possible pleiotropic agents

Liargkova

Hadjipavlou‐Litina

Koukoulitsa

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…This is in accordance with the finding of Curini et al 57 who have studied the antioxidant and LOX inhibitory activity of five natural prenyloxycarboxylic acids and showed that the most efficient LOX inhibitor (boropinic acid) is not the most active DPPH radical scavenger. Lipophilicity is referred 58 as an important physicochemical property for LOX inhibitors, and the above tested derivatives 7a and 7b seem to follow this concept (clog P 7b > clog P 7a, IC 50 7b > IC 50 7a).…”

Section: Biological Studiesmentioning

confidence: 92%

Synthesis and biological evaluation of fused oxepinocoumarins as free radicals scavengers

Litinas

Mangos

Nikkou

et al. 2011

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Lipophilicity is referred [47][48][49] as an important physichochemical property for lipoxygenase inhibition.…”

Section: Biological Studiesmentioning

confidence: 99%

Synthesis and biological evaluation of modified purine homo-N-nucleosides containing pyrazole or 2-pyrazoline moiety

Thalassitis

Katsori

Dimas

et al. 2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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9-Substituted (pyrazol-5-yl)methyl-or (2-pyrazolin-5-yl)methyl-9H-purines were synthesized from 9-allyl-6-chloro-9H-purine through the 1,3-dipolar cycloaddition reaction with nitrile imines, prepared in situ from the corresponding hydrazone and NBS/Et 3 N under MW or from hydrazinoylchloride and Et 3 N under reflux. The coupling of new 6-chloropurines with amines in H 2 O under microwaves resulted quantitatively to modified pyrazol-5-yl-or 2-pyrazolin-5-yl adenine homo-N-nucleosides. The new compounds were tested in vitro for their ability to: (i) interact with 1,1-diphenyl-2-picryl-hydrazyl (DPPH), (ii) inhibit lipid peroxidation, (iii) inhibit the activity of soybean lipoxygenase, (iv) inhibit in vitro thrombin and for (v) their antiproliferative and cytotoxic activity. Pyrazolines were found to be more potent in vitro. Compound 7a exhibited satisfactory combined antioxidant and anti-lipid peroxidation activity, inhibition of lipoxygenase (89%) and thrombin inhibitory ability, whereas compound 7b exhibited high lipoxygenase inhibitory activity in combination to significant anti-thrombin activity. No compound exhibited a significant cytotoxic activity, while all showed moderate antiproliferative activity.

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Lipoxygenase inhibitors: A comparative QSAR study review and evaluation of new QSARs

Cited by 74 publications

References 75 publications

Simple chalcones and bis-chalcones ethers as possible pleiotropic agents

Simple chalcones and bis-chalcones ethers as possible pleiotropic agents

Synthesis and biological evaluation of fused oxepinocoumarins as free radicals scavengers

Synthesis and biological evaluation of modified purine homo-N-nucleosides containing pyrazole or 2-pyrazoline moiety

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