Direct, Metal‐free C(sp2)−H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO3

Rafique, Jamal; Saba, Sumbal; Franco, Marcelo S.; Bettanin, Luana; Schneider, Alex; Silva, Lais T.; Braga, Antônio L.

doi:10.1002/chem.201705404

Cited by 110 publications

(39 citation statements)

References 108 publications

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“…All the selenylated IP were prepared from IP and diorganyl diselenides via C(sp2)‐H bond selenylation, as described previously by Rafique et al [ 29,30 ]…”

Section: Methodsmentioning

confidence: 99%

Apoptosis oxidative damage‐mediated and antiproliferative effect of selenylated imidazo[1,2‐a]pyridines on hepatocellular carcinoma HepG2 cells and in vivo

Santos

Rafique

Saba

et al. 2020

J Biochem & Molecular Tox

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Imidazo[1,2‐a]pyridines (IP) and organoselenium compounds have been widely exploited in medicinal chemistry due to their pharmacological activities. Hepatocellular carcinoma (HCC) has few treatment options, and unfortunately, the prognosis is poor. Thus, the development of novel therapeutic drugs is urgent. The present study aimed at evaluating the antitumor mechanism of selenylated IP against HepG2 cells and in vivo. The selenylated IP named IP‐Se‐06 (3‐((2‐methoxyphenyl)selanyl)‐7‐methyl‐2‐phenylimidazol[1,2‐a]pyridine) showed high cytotoxicity against HepG2 cells (half‐maximal inhibitory concentration [IC50] = 0.03 µM) and selectivity for this tumor cell line. At nontoxic concentration, IP‐Se‐06 decreased the protein levels of Bcl‐xL and increased the levels of p53, leading to inhibition of cell proliferation and apoptosis. This compound decreased the level of extracellular signal‐regulated kinase 1/2 protein and changed the levels of proteins involved in the drive of the cell cycle, tumor growth, and survival (cyclin B1, cyclin‐dependent kinase 2). In addition, IP‐Se‐06 decreased the number of cells in the S phase. In addition, IP‐Se‐06 led to increased generation of reactive oxygen species, changed antioxidant defenses, and caused DNA fragmentation. Finally, IP‐Se‐06 significantly inhibited the growth of Ehrlich ascites tumors in mice, increased survival time, and inhibited angiogenesis. Therefore, IP‐Se‐06 may be an important compound regarding the development of a therapeutic drug for HCC treatment.

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“…All the selenylated IP were prepared from IP and diorganyl diselenides via C(sp2)‐H bond selenylation, as described previously by Rafique et al [ 29,30 ]…”

Section: Methodsmentioning

confidence: 99%

Apoptosis oxidative damage‐mediated and antiproliferative effect of selenylated imidazo[1,2‐a]pyridines on hepatocellular carcinoma HepG2 cells and in vivo

Santos

Rafique

Saba

et al. 2020

J Biochem & Molecular Tox

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“…Their structure is present in many pharmaceuticals and also has applications in material sciences . Therefore, it is not surprising that the synthesis and functionalization of imidazoheteroarenes have received considerable attention in different areas of scientific research . Analogously, arylazo compounds are widely used in several areas, including the chemical industry, pharmaceuticals, chemosensors, electronics, and liquid crystals ( 1 a – d , Figure ) .…”

Section: Figurementioning

confidence: 99%

Photoinduced, Direct C(sp²)−H Bond Azo Coupling of Imidazoheteroarenes and Imidazoanilines with Aryl Diazonium Salts Catalyzed by Eosin Y

Saba

Santos

Zavarise

et al. 2020

Chemistry A European J

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Herein, a greener approach to the eosin Y‐Na2 catalyzed, C(sp2)−H bond azo coupling of imidazoheteroarene with aryl diazonium salts is described, under acid free conditions. This direct photoredox process resulted in the corresponding azo products in good to excellent yields. Besides, this new approach could also be applicable to anilines, which is a poorly reactive substrate by other methods. The main features of this reaction are that it provides high yields and is gram‐scalable and applicable to biologically relevant imidazoheteroarenes and ‐anilines.

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“…In this regard, a number of papers have pointed out the synthetic versatility of compounds termed organochalcogens [6][7][8][9][10][11][12][13]. Selenium-containing organochalcogenides seems to be of great therapeutic relevance, mostly due to the ability of these compounds to mimic natural substances with antioxidant, antitumor, antimicrobial and antiviral activities [14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Selenocyanates and Evaluation of Their Effect in Cultured Mouse Neurons Submitted to Oxidative Stress

Frizon¹,

Cararo²,

Saba³

et al. 2020

Preprint

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Herein we report the synthesis of novel selenocyanates and assessment of their effect on the oxidative challenge elicited by hydrogen peroxide (H2O2) in cultured mouse neurons. First, α-methylene-β-hydroxy esters were prepared as precursors of allylic bromides. A reaction involving the generated bromides and sodium selenocyanate was conducted to produce the desired selenocyanates (3a-f). We next prepared cultures of neurons from 7-day-old-mice (n = 36). H2O2 (10⁻5 M) was added into the culture flasks as an oxidative stress inducer, alone or combined with one of each designed compounds. PhSe)2 was used as positive control. It was carried out assessment of lipid (thiobarbituric acid reactive species, 4-hydroxy-2’-nonenal, 8-isoprostane), DNA (8-hydroxy-2’-deoxyguanosine) and protein (carbonyl) modification parameters. Finally, catalase and superoxide dismutase activities were also evaluated. Among the compounds, 3b, 3d and 3f exhibited the most pronounced pattern of antioxidant activity, similar to (PhSe)2. These novel aromatic selenocyanates could be promising to be tried in most sophisticated in vitro studies or even at preclinical level.

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Direct, Metal‐free C(sp²)−H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO₃

Cited by 110 publications

References 108 publications

Apoptosis oxidative damage‐mediated and antiproliferative effect of selenylated imidazo[1,2‐a]pyridines on hepatocellular carcinoma HepG2 cells and in vivo

Apoptosis oxidative damage‐mediated and antiproliferative effect of selenylated imidazo[1,2‐a]pyridines on hepatocellular carcinoma HepG2 cells and in vivo

Photoinduced, Direct C(sp²)−H Bond Azo Coupling of Imidazoheteroarenes and Imidazoanilines with Aryl Diazonium Salts Catalyzed by Eosin Y

Synthesis of Novel Selenocyanates and Evaluation of Their Effect in Cultured Mouse Neurons Submitted to Oxidative Stress

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Direct, Metal‐free C(sp2)−H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO3

Cited by 110 publications

References 108 publications

Apoptosis oxidative damage‐mediated and antiproliferative effect of selenylated imidazo[1,2‐a]pyridines on hepatocellular carcinoma HepG2 cells and in vivo

Apoptosis oxidative damage‐mediated and antiproliferative effect of selenylated imidazo[1,2‐a]pyridines on hepatocellular carcinoma HepG2 cells and in vivo

Photoinduced, Direct C(sp2)−H Bond Azo Coupling of Imidazoheteroarenes and Imidazoanilines with Aryl Diazonium Salts Catalyzed by Eosin Y

Synthesis of Novel Selenocyanates and Evaluation of Their Effect in Cultured Mouse Neurons Submitted to Oxidative Stress

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Direct, Metal‐free C(sp²)−H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO₃

Photoinduced, Direct C(sp²)−H Bond Azo Coupling of Imidazoheteroarenes and Imidazoanilines with Aryl Diazonium Salts Catalyzed by Eosin Y