Molecular characterization of EP6—A novel imidazo[1,2-a]pyridine based direct 5-lipoxygenase inhibitor

Wiśniewska, Joanna; Rödl, Carmen B.; Kahnt, Astrid S.; Buscató, Estel la; Ulrich, S.; Tanrıkulu, Yusuf; Achenbach, Janosch; Rörsch, Florian; Grösch, Sabine; Schneider, Gisbert; Cinatl, Jindrich; Proschak, Ewgenij; Steinhilber, Dieter

doi:10.1016/j.bcp.2011.10.012

Cited by 25 publications

(12 citation statements)

References 71 publications

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“…1 H and 13 C NMR spectra were run on a Bruker FT-400 in CDCl 3 , using TMS as an internal standard. IR spectra were recorded on a Shimadzu 470 spectrophotometer (KBr disks).…”

Section: Chemistrymentioning

confidence: 99%

“…Experimental details and 1 H and 13 C NMR spectra are available, via the supplementary content section of this article's web page.…”

Section: Supporting Informationmentioning

confidence: 99%

“…A part of attentions has been focused on small molecules containing fused heterocyclic systems including indolizine 9,10 and imidazo-fused heterocycles 11,12 previously described (I, Figure 1) as a potential inhibitors of 15-LOX. In a study by Wisniewska et al, imidazo[1,2-a]pyridine-3-yl-amine analog (EP6, II) was evaluated as a 5-LOX inhibitor 13 . On the other hand, a series of quinolinebased compounds were reported as potent inhibitors of LOX [14][15][16][17][18] .…”

Section: Introductionmentioning

confidence: 99%

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Quinoline-based imidazole-fused heterocycles as new inhibitors of 15-lipoxygenase

Dianat

Moghimi

Mahdavi

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of 2-chloro-quinoline-based imidazopyridines 6a-l and imidazothiazoles 6m-o bearing a bulky alkylamine side chain were synthesized as soybean 15-LOX inhibitors. The target compounds 6a-o were prepared via one-pot reaction of 2-chloroquinoline-3-carbaldehyde (3), heteroaromatic amidine 4, and alkyl isocyanides 5, in the presence of NH 4 Cl. All compounds showed significant anti-15-LOX activity (IC 50 values 40 mM). Among the title compounds, the imidazo[2,1-b]thiazole derivative 6n bearing a tert-butylamine moiety showed the highest activity against soybean 15-LOX enzyme.

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“…1 H and 13 C NMR spectra were run on a Bruker FT-400 in CDCl 3 , using TMS as an internal standard. IR spectra were recorded on a Shimadzu 470 spectrophotometer (KBr disks).…”

Section: Chemistrymentioning

confidence: 99%

“…Experimental details and 1 H and 13 C NMR spectra are available, via the supplementary content section of this article's web page.…”

Section: Supporting Informationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Quinoline-based imidazole-fused heterocycles as new inhibitors of 15-lipoxygenase

Dianat

Moghimi

Mahdavi

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In the past few years a growing interest in the chemistry of imidazo[1,2-a] pyridines and isoquinolines has been developed due to the extent of their applications in pharmacological science (Wisniewska et al, 2012;Hayakawa et al, 2007;Singhaus et al, 2010). Indeed they are known for their antibacterial (Al-Tel et al, 2011), antiviral (Gueiffier et al, 1996,1998), anti-inflammatory (Flores et al, 2012, antiulcer (Katsura et al,1992), antitubercular (Moraski et al, 2012), anticancer (Ducray et al, 2011, antiparasitic (Martı´nez et al, 2010) and antiprotozoa (Ismail et al, 2004) activities.…”

Section: Introductionmentioning

confidence: 99%

Polar [3 + 2] cycloaddition of isatin-3-imines with electrophilically activated heteroaromatic N-ylides: Synthesis of spirocyclic imidazo[1,2-a]pyridine and isoquinoline derivatives

Mokhtari

Seifi

Saheb

et al. 2019

Arabian Journal of Chemistry

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A new synthesis of spiro[imidazo[1,2-a]pyridine-2,3 0 -indoline]-2 0 -ones 3a-f and spiro[imidazo[1,2-a]isoquinoline-2,3 0 -indolin]-2 0 -ones 5a-d, respectively by polar [3 + 2] cycloaddition reactions of isatin-3-imines with pyridinium and isoquinolinium ylides which are derived from 2-bromoacetophenone, 2,4 0 -dibromoacetophenone or methyl bromoacetate is described. These cycloaddition reactions consist of the nucleophilic attack of the heteroaromatic N-ylides on isatin-3-imine derivatives. The salient features of these processes include operational simplicity, high yields, and easily accessible starting materials. In addition, Density Functional Theory (DFT) calculations at the M06-2X/6-31 + G(d) level have been performed to investigate the possible transition states and products. The theoretical results are in good agreement with the experimental findings and show that the product 3a is the most stable product and is formed through a kinetically feasible pathway. ª 2015 The Authors. Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

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“…[7] Moreover, a series of novel 21 compounds based on a central imidazo[1,2-a]pyridine scaffold that exhibit promising inhibitory potential towards kinases have been reported. [8][9][10] Due to the increased interest in this class of compounds, efficient synthetic methods are in increasing demand.…”

mentioning

confidence: 99%

9,11,12,14‐Tetraaryldibenzo[f,h]imidazo[1,2‐b]isoquinolines and Their Emission Responses to Solvent Polarity, Acidity, and Nitroarenes

et al. 2013

Eur J Org Chem

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9,11,12,14‐Tetraaryldibenzo[f,h]imidazo[1,2‐b]isoquinolines 3a–h were synthesized in moderate yields through the reaction of benzils with 1,3‐diphenyl‐2H‐cyclopenta[l]phenanthren‐2‐ones and ammonium acetate. The photophysical properties of the products in solutions and in thin films were investigated, and strong emissions ranging from 492 to 516 nm were observed in cyclohexane solutions. Moreover, 3h exhibited potential as a versatile fluorescent chemosensor for the detection of solvent polarity, acidity, or trace amounts of nitroaromatics.

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Molecular characterization of EP6—A novel imidazo[1,2-a]pyridine based direct 5-lipoxygenase inhibitor

Cited by 25 publications

References 71 publications

Quinoline-based imidazole-fused heterocycles as new inhibitors of 15-lipoxygenase

Quinoline-based imidazole-fused heterocycles as new inhibitors of 15-lipoxygenase

Polar [3 + 2] cycloaddition of isatin-3-imines with electrophilically activated heteroaromatic N-ylides: Synthesis of spirocyclic imidazo[1,2-a]pyridine and isoquinoline derivatives

9,11,12,14‐Tetraaryldibenzo[f,h]imidazo[1,2‐b]isoquinolines and Their Emission Responses to Solvent Polarity, Acidity, and Nitroarenes

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