Synthesis of new ibuprofen derivatives with their in silico and in vitro cyclooxygenase-2 inhibitions

Hızlıateş, Cevher Gündoğdu; Alyürük, Hakan; Gocmenturk, Mustafa; Ergün, Yavuz; Çavaş, Levent

doi:10.1016/j.bioorg.2013.10.002

Cited by 22 publications

(7 citation statements)

References 59 publications

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“…Previously, Hizliates et al, performed an in-silico and in-vitro molecular docking analysis of ligands derived from Ibuprofen for the inhibition of COX-2. However, they did not perform in-silico analysis as thoroughly as done in this study, such as testing for drug-likeliness and ADMET properties 25 . Bitten court et al, have also reported a similar study in which they present a comparison of the properties of ibuprofen to that of two benzoyl propionic acid derivatives.…”

Section: Fig 1: Molecular Structure Of the (2s) -2-[4-(2-oxo-2 5-dimentioning

confidence: 99%

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2020

IJPSR

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Section: Fig 1: Molecular Structure Of the (2s) -2-[4-(2-oxo-2 5-dimentioning

confidence: 99%

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2020

IJPSR

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“…Its 5-hour reaction mixture has been re luxed. The solids gained by iltration and recrystallized by ethanol forward to cooling, The percent of yield, physical properties and RF values present in the Table 2 (Gundogdu-Hizliates et al, 2014).…”

Section: Synthesis Of the Compound(e)-n'-benzylidene-2-(4-isobutylphementioning

confidence: 99%

Synthesis, characterization and pharmacological activity of Ibuprofen Acyl Hydrazones and their Conversion into 1,3,4-Oxadiazoline Derivatives

Alderawy

Alrubaie

Sheri

et al. 2019

ijrps

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This work implicates the synthesis of Ibuprofen Acyl Hydrazones and then Converted into the new 1,3,4-Oxadiazoline derivatives that characterized by proton-NMR, FT.IR and elemental microanalysis (CHN) techniques. The intermediates and final compounds were investigated for their physicochemical properties, including the melting point, color, the yield percent, and thin-layer chromatography performed by using TLC silica gel (60) F254, Merck (Germany), to identify the purity of the products and to know the reaction endpoint. Compounds were monitored by UV light irradiation and the elution by using the following systems:: ethyl acetate: hexane ( 3:7), ethyl acetate, ethanol:dioxan (1:1) and methanol: chloroform (1:9). The study was performed using Swiss albino mice (25-30 g) for the pharmacological activity assessment. Hind edema template of carrageenan used for anti-inflammatory activity assessment and the analgesic activity evaluated using ( writhing induced by acetic acid ) and hot plate method, the results show that all the final compounds present with good anti-inflammatory plus analgesic activities exhibited in the animal model of our experimental work , we observed that the standard compound and the synthesized derivatives substantially reduced carrageenan-induced edema at all-times (2,4,6,24) hours, all chemically synthesized new compounds actually significantly reduced the number of acetic acid writhings induced in mice and finally in hot plate method there is high increase in the reaction time to painful stimulation

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“…Another example of groups showing valuable COX‐2 inhibitory potential is acyl hydrazone sulfonamide and its derivatives containing acyl sulfonamide [8] . Among the newly published research on selective COX‐2 inhibitors, N ‐acyl hydrazones, as a new class of anti‐inflammatory compounds, have shown great promise in terms of selectivity in COX‐2 binding and anti‐inflammatory activity [9–12] . It is also known that the methyl sulfonyl group enhances selective COX‐2 inhibition [13–20] …”

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confidence: 99%

Design, Synthesis and Biological Evaluation of New N‐Acyl Hydrazones with a Methyl Sulfonyl Moiety as Selective COX‐2 Inhibitors

Osmaniye

Sağlık

Levent

et al. 2021

Chemistry & Biodiversity

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The mechanism of action of nonsteroidal anti‐inflammatory drugs (NSAIDs) is inhibition of specific prostaglandin (PG) synthesis by inhibition of cyclooxygenase (COX) enzymes. The two COX isoenzymes show 60 % similarity. It is known that the nonspecific side effects of conventional NSAIDs are physiologically caused by inhibition of the COX‐1 enzyme. Therefore, the use of COX‐2 selective inhibitors is seen to be a more beneficial approach in reducing these negative effects. However, some of the existing COX‐2 selective inhibitors show cardiovascular side effects. Therefore, studies on the development of new selective COX‐2 inhibitors remain necessary. It is important to develop new COX‐2 inhibitors in the field of medicinal chemistry. Accordingly, novel N‐acyl hydrazone derivatives were synthesized as new COX‐2 inhibitors in this study. The hydrazone structure, also known for its COX activity, is important in terms of many biological activities and was preferred as the main structure in the design of these compounds. A methyl sulfonyl pharmacophore was added to the structure in order to increase the affinity for the polar side pocket present in the COX‐2 enzyme. It is known that methyl sulfonyl groups are suitable for polar side pockets. The synthesis of the compounds (3a–3j) was characterized by spectroscopic methods. Evaluation of in vitro COX‐1/COX‐2 enzyme inhibition was performed by fluorometric method. According to the enzyme inhibition results, the obtained compounds displayed the predicted selectivity for COX‐2 enzyme inhibition. Compound 3j showed important COX‐2 inhibition with a value of IC50=0.143 uM. Interaction modes between the COX‐2 enzyme and compound 3j were investigated by docking studies.

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Synthesis of new ibuprofen derivatives with their in silico and in vitro cyclooxygenase-2 inhibitions

Cited by 22 publications

References 59 publications

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Synthesis, characterization and pharmacological activity of Ibuprofen Acyl Hydrazones and their Conversion into 1,3,4-Oxadiazoline Derivatives

Design, Synthesis and Biological Evaluation of New N‐Acyl Hydrazones with a Methyl Sulfonyl Moiety as Selective COX‐2 Inhibitors

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