Xanthine oxidase inhibitory properties and anti-inflammatory activity of 2-amino-5-alkylidene-thiazol-4-ones

Smelcerovic, Zaklina; Veljković, Andrej; Kocić, Gordana; Yancheva, Denitsa; Petronijević, Živomir; Anderluh, Marko; Šmelcerović, Andrija

doi:10.1016/j.cbi.2015.01.022

Cited by 40 publications

(19 citation statements)

References 29 publications

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“…Accordingly, it was ascertained that AR inhibition prevents multiple inflammatory pathways [379e381] and, therefore, new more effective and safer AR inhibitors were designed not only as antidiabetic (see above) but also antinflammatory agents [232] (peripheral blood mononuclear cells) exerted through the NF-kB inhibition. This and related compounds also had antioxidant activity and xanthine oxidase inhibitory potency [152]. Among 5-arylidenerhodanine derivatives the first small molecule able to inhibit HIV replication by targeting a cellular enzyme e the RNA helicases DDX3 had been identified [385].…”

Section: Anti-inflammatory Agentsmentioning

confidence: 99%

“…Interpretation of 5-arylidene-4-thiazolidinones as frequent hitters is often not confirmed in experimental studies [24,151,152] and a large number of lead-compounds belong to 5-ene-4thiazolidinones. The positive perspective may also be associated with the polypharmacological approach in drug discovery, where the affinity toward various targets is regarded as an advantage [14].…”

Section: Pharmacological Profiles Of 5-ene-4-thiazolidinonesmentioning

confidence: 99%

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5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

151

133

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The presented review is an attempt to summarize a huge volume of data on 5-ene-4-thiazolidinones being a widely studied class of small molecules used in modern organic and medicinal chemistry. The manuscript covers approaches to the synthesis of 5-ene-4-thiazolidinone derivatives: modification of the C5 position of the basic core; synthesis of the target compounds in the one-pot or multistage reactions or transformation of other related heterocycles. The most prominent pharmacological profiles of 5-ene derivatives of different 4-thiazolidinone subtypes belonging to hit-, lead-compounds, drug-candidates and drugs as well as the most studied targets have been discussed. Currently target compounds (especially 5-en-rhodanines) are assigned as frequent hitters or pan-assay interference compounds (PAINS) within high-throughput screening campaigns. Nevertheless, the crucial impact of the presence/nature of C5 substituent (namely 5-ene) on the pharmacological effects of 5-ene-4-thiazolidinones was confirmed by the numerous listed findings from the original articles. The main directions for active 5-ene-4-thiazolidinones optimization have been shown: i) complication of the fragment in the C5 position; ii) introduction of the substituents in the N3 position (especially fragments with carboxylic group or its derivatives); iii) annealing in complex heterocyclic systems; iv) combination with other pharmacologically attractive fragments within hybrid pharmacophore approach. Moreover, the utilization of 5-ene-4-thiazolidinones in the synthesis of complex compounds with potent pharmacological application is described. The chemical transformations cover mainly the reactions which involve the exocyclic double bond in C5 position of the main core and correspond to the abovementioned direction of the 5-ene-4-thiazolidinone modification.

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Section: Anti-inflammatory Agentsmentioning

confidence: 99%

Section: Pharmacological Profiles Of 5-ene-4-thiazolidinonesmentioning

confidence: 99%

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Kaminskyy

Kryshchyshyn

Lesyk

2017

European Journal of Medicinal Chemistry

151

133

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“…Therefore, identifying some novel non-purine XO inhibitors with potent XO inhibitory potency and fewer side effects is extremely necessary. In fact, some excellent non-purine XO inhibitors have been reported in the recent literature, including carboxyl moiety containing inhibitors, such as Febuxostat [5], Y-700 [6], selenazoles [7], isoxazoles [8] and 2-(indol-5-yl)thiazoles [9]; and non-carboxyl moiety containing inhibitors, like Topiroxostat [10], isocytosines [11e13], N-(1,3-diaryl-3-oxopropyl)amides [14], N-1-acetyl-3,5-diaryl-4,5-dihydro-(1H) pyrazoles [15], naphthoflavones [16], 2-amino-5-alkylidene-thiazol-4-ones [17], azaflavones [18], naphthopyrans [19], 4,6-diaryl/ heteroarylpyrimidin-2(1H)-ones [20], and 2,4-diaryl-pyrano [3,2-c] chromen-5(4H)-one [21] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of 1-hydroxy/methoxy-4-methyl-2-phenyl-1H-imidazole-5-carboxylic acid derivatives as non-purine xanthine oxidase inhibitors

Chen

Zhang

Wang

et al. 2015

European Journal of Medicinal Chemistry

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“…A series of 30 derivatives of 2‐amino‐5‐alkylidene‐thiazol‐4‐ones 175 , obtained by combining six different substituents at position 5 (R 1 ) with five different amines at position 2 (R 2 ) of the thiazole‐4‐one ring, were tested against both bovine milk and rat liver XO . Only compounds showing more than 50 % inhibition at a concentration of 50 μg mL −1 were selected for further studies to determine their IC 50 values.…”

Section: Non‐purine‐like Inhibitors Of Xomentioning

confidence: 99%

Inhibitors of Xanthine Oxidase: Scaffold Diversity and Structure‐Based Drug Design

2019

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Xanthine oxidase (XO) is the enzyme responsible for the catabolism of purines and their conversion into uric acid. XO is thus the target for the treatment of hyperuricemia and gout. For more than 50 years the only XO inhibitor drug available on the market was the purine analogue allopurinol. In the last decade there has been a resurgence in the search for new inhibitors of XO, as the activity of XO and hyperuricemia have also been associated with a variety of conditions such as diabetes, hypertension, and other cardiovascular diseases. In recent years the non‐purine inhibitor febuxostat was approved in Europe and the USA for the treatment of hyperuricemia. This drug was followed by another XO inhibitor called topiroxostat. This review discusses the molecular structures and activities of the multiple classes of inhibitors that have been developed since the discovery of allopurinol, with a brief review of the molecular interactions between inhibitors and XO active site residues for the most important molecules. The challenges ahead for the discovery of new inhibitors of XO with novel chemical structures are discussed.

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Xanthine oxidase inhibitory properties and anti-inflammatory activity of 2-amino-5-alkylidene-thiazol-4-ones

Cited by 40 publications

References 29 publications

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

5-Ene-4-thiazolidinones – An efficient tool in medicinal chemistry

Synthesis and evaluation of 1-hydroxy/methoxy-4-methyl-2-phenyl-1H-imidazole-5-carboxylic acid derivatives as non-purine xanthine oxidase inhibitors

Inhibitors of Xanthine Oxidase: Scaffold Diversity and Structure‐Based Drug Design

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