Synthesis and antiproliferative activities of quebecol and its analogs

Pericherla, Kasiviswanadharaju; Shirazi, Amir Nasrolahi; Rao, V. Kameshwara; Tiwari, Rakesh; DaSilva, Nicholas A.; McCaffrey, Kellen; Beni, Yousef A.; González‐Sarrías, Antonio; Seeram, Navindra P.; Parang, Keykavous; Kumar, Anil

doi:10.1016/j.bmcl.2013.07.058

Cited by 17 publications

(13 citation statements)

References 11 publications

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“…For example, quebecol is a phenolic compound from maple syrup 27 that possesses anti-inflammatory 28 and anti-proliferative properties. 29 A variety of phenolic derivatives from maple syrup demonstrate free radical scavenging activity superior to that of vitamin C. 3 Several polyphenolic molecules present in maple syrup show anti-proliferative effects through arresting cell cycles, suggesting potential effects in cancer prevention. 30 In addition, in vivo studies on phenolic-enriched maple syrup extracts have shown promising therapeutic potential for liver protection, 31 anti-inflammation 32 and anti-diabetes.…”

Section: Resultsmentioning

confidence: 99%

Detection of Inulin, a Prebiotic Polysaccharide, in Maple Syrup

Sun

Seeram

et al. 2016

J. Agric. Food Chem.

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Maple syrup is a widely consumed plant-derived natural sweetener produced by concentrating xylem sap collected from certain maple (Acer) species. During thermal evaporation of water, natural phytochemical components are concentrated in maple syrup. The polymeric components from maple syrup were isolated by ethanol precipitation, dialysis, and anion exchange chromatography and structurally characterized by glycosyl composition analysis, glycosyl linkage analysis, and nuclear magnetic resonance spectroscopy. Among the maple syrup polysaccharides, one neutral polysaccharide was characterized as inulin with a broad molecular weight distribution, representing the first isolation of this prebiotic carbohydrate from a xylem sap. In addition, two acidic polysaccharides with structural similarity were identified as arabinogalactans derived from rhamnogalacturonan type I pectic polysaccharides.

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Section: Resultsmentioning

confidence: 99%

Detection of Inulin, a Prebiotic Polysaccharide, in Maple Syrup

Sun

Seeram

et al. 2016

J. Agric. Food Chem.

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“…e reaction mixture was stirred for 24 hours at room temperature, the solvent was removed in vacuum, and the residue was washed with diethyl ether and dried in vacuum. (6-hydroxybenzo[d] [1,3] (6-hydroxybenzo[d] [1,3] (6-hydroxybenzo[d] [1,3] [4]resorcinarenes 10a,d [27,41]. To a mixture of 1.25 mmol pyrrolidine-1carboxamide 1 and appropriate 0.16 g (1.25 mmol) 2methylresorcinol in 5 ml dry chloroform, 2 ml trifluoroacetic acid was added.…”

Section: General Methods For the Synthesis Of Diarylbutanesmentioning

confidence: 99%

“…Diarylmethane derivatives containing two phenolic moieties are of interest due to their wide spectrum biological activity. ese compounds are known to inhibit C-C chemokine receptors [1], possess anti-inflammatory [2], antiproliferative [3], antimicrobial [4], anti-HIV [5], and anticancer activity [6]. Some compounds of this class exhibit antibacterial properties [7,8].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Novel Dibenzoxanthenes, Diarylbutanes, and Calix[4]resorcinarenes via Consecutive Pyrrolidine Ring-Closure/Ring-Opening Reactions

Smolobochkin

Газизов

Бурилов

et al. 2019

Journal of Chemistry

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Herein, we report the approach to the otherwise hardly accessible dibenzoxanthenes, diarylbutanes, and calix[4]resorcinarenes possessing urea moieties based on the reaction of N-(4,4-diethoxybutyl)ureas with electron-rich aromatics in strongly acidic media. Unlike the previously developed methods, the proposed approach benefits from one-pot procedure and allows to obtain the target compounds with much higher yields.

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“…图 3 机理探索实验 Figure 3 Experiments for probing the reaction mechanism 5). 传统合成方法路线较长 [24] , 或需要 -78 ℃的低温条件 [25] . 本路线合成步骤少, 原料简单易得, 条件温和, 操作更简便.…”

Section: 引言unclassified

Ni-Catalysed Regioselective α,β-Diarylation of α,β-Unsaturated Aldehydes

Xie¹,

Zeng²,

Luo³

2021

Acta Chimica Sinica

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Three-component difunctionalization reaction is one of the most important ways to construct C-C bond or C-X bond in organic chemistry. It has the characteristics of high efficiency by introducing two new chemical bonds into the substrate at the same time. Most current reports on the difunctionalization follow the interest of unsaturated bonds such as olefins. Olefins exist in many natural products and play an important role in organic synthesis, and they are widely used in pharmaceutical manufacture, chemical industry and experimental study. Therefore, the study on the difunctionalization reaction of olefins is of a great potential application. In this paper, we report an α,β-diarylation reaction of α,β-unsaturated aldimines with Ni(COD)2 as catalyst, and aryl magnesium bromides and aryl bromides as the arylating reagents. This method offers a new straightforward strategy to introduce two different aryls concurrently and provides a readily access to various triphenyl-substituted propionaldehydes. Moreover, the synthesis of natural product Quebecol (2,3,3-tri-(3-methoxy-4hydroxyphenyl)propan-1-ol) can be realized by using the established reaction as the core step. Mechanistic studies revealed that the reaction underwent a process of nucleophilic addition, metal exchange and reductive elimination. A general procedure of this nickel-catalyzed diarylation is as follows: To a 25 mL Schlenk tube equipped with a magnetic stir bar were added an aldimine (0.20 mmol), aryl bromide (0.40 mmol), PPh3 (0.04 mmol, 20 mol%) and Ni(COD)2 (0.02 mmol, 10 mol%). After being evacuated and backfilled with nitrogen for three times, dry THF (1.6 mL) and aromatic Grignard reagent (0.4 mL, 1.0 mol/L in THF, 0.40 mmol) were added to the tube. The reaction mixture was stirred at 80 ℃ under an nitrogen atmosphere for 12 h and quenched with 3 mol/L HCl (aq.). The mixture was extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to afford the desired triphenyl-substituted propionaldehydes.

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Synthesis and antiproliferative activities of quebecol and its analogs

Cited by 17 publications

References 11 publications

Detection of Inulin, a Prebiotic Polysaccharide, in Maple Syrup

Detection of Inulin, a Prebiotic Polysaccharide, in Maple Syrup

One-Pot Synthesis of Novel Dibenzoxanthenes, Diarylbutanes, and Calix[4]resorcinarenes via Consecutive Pyrrolidine Ring-Closure/Ring-Opening Reactions

Ni-Catalysed Regioselective α,β-Diarylation of α,β-Unsaturated Aldehydes

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