Oxidative coupling of 4-substituted 2-methoxy phenols using methyltributylammonium permanganate in dichloromethane

Marques, Francisco A.; Simonelli, Fábio; Oliveira, Alfredo R. M. de; Gohr, G. L.; Leal, Paulo César

doi:10.1016/s0040-4039(97)10665-7

Cited by 30 publications

(17 citation statements)

References 6 publications

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“…Synthesis of dieugenol ( 1 ) was performed by oxidative dimerization of eugenol ( 4 ) (Sigma-Aldrich, Germany) as described by Ogata et al (2000) and Marque et al, (1998). After recrystallization from 2-propanol, isolated 1 was analyzed by NMR (H-NMR purity >99%).…”

Section: Methodsmentioning

confidence: 99%

Computer-Aided Discovery, Validation, and Mechanistic Characterization of Novel Neolignan Activators of Peroxisome Proliferator-Activated Receptor γ

Fakhrudin¹,

Ladurner²,

Atanasov³

et al. 2010

Mol Pharmacol

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Peroxisome proliferator-activated receptor gamma (PPAR␥) agonists are used for the treatment of type 2 diabetes and metabolic syndrome. However, the currently used PPAR␥ agonists display serious side effects, which has led to a great interest in the discovery of novel ligands with favorable properties. The aim of our study was to identify new PPAR␥ agonists by a PPAR␥ pharmacophore-based virtual screening of 3D natural product libraries. This in silico approach led to the identification of several neolignans predicted to bind the receptor ligand binding domain (LBD). To confirm this prediction, the neolignans dieugenol, tetrahydrodieugenol, and magnolol were isolated from the respective natural source or synthesized and subsequently tested for PPAR␥ receptor binding. The neolignans bound to the PPAR␥ LBD with EC 50 values in the nanomolar range, exhibiting a binding pattern highly similar to the clinically used agonist pioglitazone. In intact cells, dieugenol and tetrahydrodieugenol selectively activated human PPAR␥-mediated, but not human PPAR␣-or -␤/␦-mediated luciferase reporter expression, with a pattern suggesting partial PPAR␥ agonism. The coactivator recruitment study also demonstrated partial agonism of the tested neolignans. Dieugenol, tetrahydrodieugenol, and magnolol but not the structurally related eugenol induced 3T3-L1 preadipocyte differentiation, confirming effectiveness in a cell model with endogenous PPAR␥ expression. In conclusion, we identified neolignans as novel ligands for PPAR␥, which exhibited interesting activation profiles, recommending them as potential pharmaceutical leads or dietary supplements.Western lifestyle with a high intake of simple sugars, saturated fat, and physical inactivity promotes pathologic conditions such as type 2 diabetes, obesity, and metabolic syndrome, which are currently taking a devastating epidemical spread worldwide. Compounds that are activating PPAR␥ may help to fight these pathological conditions (Cho and Momose, 2008).PPARs are ligand-activated transcription factors belonging to the nuclear receptor superfamily, and their main function relates to the regulation of genes involved in glucose and lipid metabolism (Tenenbaum et al., 2003;Desvergne et al., 2006). Three isoforms of this nuclear receptor have been identified so far: PPAR␣, PPAR␤/␦, and PPAR␥. PPAR␣ is highly expressed in skeletal muscle, liver, kidney, heart, and the vascular wall, and it was shown to be mainly involved in the regulation of lipid catabolism (Fruchart, 2009). PPAR␥ is

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Section: Methodsmentioning

confidence: 99%

Computer-Aided Discovery, Validation, and Mechanistic Characterization of Novel Neolignan Activators of Peroxisome Proliferator-Activated Receptor γ

Fakhrudin¹,

Ladurner²,

Atanasov³

et al. 2010

Mol Pharmacol

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“…As a result of these pharmacological applications, a range of efforts has been undertaken to produce DHDE, which can be prepared by oxidative coupling reaction of eugenol , biotransformation in vegetal cell cultures , radical reactions , conventional synthesis , and enzymatic biotransformation using peroxidases .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antileishmanial Activity of Natural Dehydrodieugenol and Its Mono‐ and Dimethyl Ethers

Rodrigues

Barbosa-Filho

Oliveira

et al. 2016

Chemistry & Biodiversity

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The study of chemistry of naturally occurring compounds and the synthesis of their derivatives is fundamentally important for the development of new drugs. In this work, dehydrodieugenol (DHDE) was obtained through oxidative coupling of eugenol, promoted by an aqueous mixture of potassium ferricyanide (K3 [Fe(CN)6 ]) and NH3 · H2 O. The partial methoxylation of DHDE with MeI and K2 CO3 mainly resulted in the molecular-shaped monomethyl ether (DHDE-1MeO) and its dimethyl ether derivative (DHDE-2MeO). The products from the reactions were characterized by (1) H- and (13) C-NMR spectroscopy. Additionally, these studies have reported the antileishmanial activity of DHDE against Leishmania amazonensis (IC50 value of 42.20 μg ml(-1) ) and shown that partial methoxylation of DHDE results in a significant increase in its antiparasitic activity (IC50 value of 13.68 μg ml(-1) ). Based on in vitro bioassays, DHDE-1MeO has shown the highest leishmanicidal activity in promastigota form. Production by direct one-step synthesis of this monomethoxylated compound can be considered to be a cost-effective and environmentally friendly method with a short reaction time.

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“…[5,6] Pd/C, Ru/C, and Pt/C catalysts provided hydrocarbons in excellent yields with the simultaneous production of methanol under optimized conditions (water, 1 % H 3 PO 4 , 4 MPa H 2 , 523 K, 30 min). Typical dimer compounds including a-O-4 dimer and 5-5 dimer (Scheme 3) were then synthesized according to a reported method [10] to test the possibility of protecting the CÀC linkages. The dimer a-O-4 is cleaved into two parts to give three C 7 -C 9 hydrocarbons in a total yield of 93.6 mol % and methanol (99.0 mol %; Table 3).…”

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confidence: 99%

Selective Degradation of Wood Lignin over Noble‐Metal Catalysts in a Two‐Step Process

et al. 2008

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Breaking down is usually hard to do…︁ The direct conversion of lignin into alkanes and methanol was carried out in a two‐step process (hydogenolysis and hydrogenation) involving initial treatment of white birch wood sawdust with H2 in dioxane/water/phosphoric acid using Rh/C as the catalyst. The resulting monomers and dimers obtained by selective CO hydrogenolysis were then hydrogenated in near‐critical water employing Pd/C as the catalyst.

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Oxidative coupling of 4-substituted 2-methoxy phenols using methyltributylammonium permanganate in dichloromethane

Cited by 30 publications

References 6 publications

Computer-Aided Discovery, Validation, and Mechanistic Characterization of Novel Neolignan Activators of Peroxisome Proliferator-Activated Receptor γ

Computer-Aided Discovery, Validation, and Mechanistic Characterization of Novel Neolignan Activators of Peroxisome Proliferator-Activated Receptor γ

Synthesis and Antileishmanial Activity of Natural Dehydrodieugenol and Its Mono‐ and Dimethyl Ethers

Selective Degradation of Wood Lignin over Noble‐Metal Catalysts in a Two‐Step Process

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