A Re-Investigation of Resveratrol Synthesis of Perkins Reaction. Application to the Synthesis of Aryl Cinnamic Acids.

Solladié, Guy; Pasturel‐Jacope, Yacine; Maignan, Jean

doi:10.1002/chin.200333105

Cited by 2 publications

(2 citation statements)

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“…tert-butyl (S)-3-methylpiperazine-1-carboxylate was undertaken)[18] and alkylation of the free piperazine nitrogen where required was completed by reductive amination with the requisite aliphatic aldehyde to generate the tertiary amine prior to base hydrolysis[19] to liberate the capping group.…”

Section: Synthesis Of Benzoic Acid Derived N-terminal Capping Groupsmentioning

confidence: 99%

Benzamide capped peptidomimetics as non-ATP competitive inhibitors of CDK2 using the REPLACE strategy

Premnath

Craig

Liu

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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Inhibition of Cyclin Dependent Kinase 2 (CDK2) in complex with cyclin A in G1/S phase of the cell cycle has been shown to promote selective apoptosis of cancer cells through the E2F1 pathway. An alternative approach to catalytic inhibition is to target the substrate recruitment site also known as the cyclin binding groove (CBG) to generate selective non-ATP competitive inhibitors. The REPLACE strategy has been applied to identify fragment alternatives and substituted benzoic acid derivatives were evaluated as a promising scaffold to present appropriate functionality to mimic key peptide determinants. Fragment Ligated Inhibitory Peptides (FLIPs) are described which potently inhibit both CDK2/cyclin A and CDK4/cyclin D1 and have preliminary anti-tumor activity. A structural rationale for binding was obtained through molecular modeling further demonstrating their potential for further development as next generation non ATP competitive CDK inhibitors.

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Section: Synthesis Of Benzoic Acid Derived N-terminal Capping Groupsmentioning

confidence: 99%

Benzamide capped peptidomimetics as non-ATP competitive inhibitors of CDK2 using the REPLACE strategy

Premnath

Craig

Liu

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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“…This necessitates the development of alternative chemical and biocatalytic strategies for the synthesis and modifications of resveratrol. The chemical synthesis of resveratrol is carried out by the Perkin reaction (Solladie et al, 2003), Wittig reaction, Horner -Wadsworth-Emmons reaction (Yu et al, 2002), or the Heck reaction (Botella and Najera, 2004), which requires the use of expensive and often toxic reagents. As in the case of bioconversion, genetically modified microorganisms or plant cell cultures are employed in the synthesis of resveratrol (Jeandet et al, 2014;Horinouchi, 2009;Kang et al, 2014;Rimando et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Biomodifications of resveratrol by Phanerochaete chrysosporium

Brzezińska-Rodak

Lubiak

Klimek‐Ochab

et al. 2019

bta

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Compounds of plant origin showing antioxidative activity are important due to their ability to decrease oxidative stress. They also protect against the harmful effects of the free radicals formed as by-products of some metabolic pathways or as external factors. This supports the application of these compounds (e.g., vitamin C) as additives of food, pharmaceuticals (vitamin E, curcumin, etc.), and cosmetics (e.g., ellagic acid). Natural antioxidants are mainly isolated from plant sources, but besides these, novel, effective, and "green" methods of obtaining antioxidative compounds are being investigated. One of the natural antioxidants is resveratrol belonging to the stilbene polyphenol family. It occurs naturally in grape, and is produced by cells in response to fungal infections or a potential stress factor (e.g., tissue damage). The beneficial effect of resveratrol is based on the inhibition of lipid oxidation and cardioprotective properties. The biocatalyzed synthesis of O -methylated derivatives of resveratrol is especially interesting from the point of view of their possible applications as anticancer agents. The fungal species Phanerochaete chrysosporium is known for its ability to produce methyltransferases, and therefore used as a biocatalyst in resveratrol modifications. Increased production of methyltransferase was stimulated in the strain by changing the conditions of both its cultivation and biotransformation. However, such an approach resulted in the conversion of resveratrol into 3,5-dihydroxybenzaldehyde, indicating a partial degradation of the substrate.

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A Re-Investigation of Resveratrol Synthesis of Perkins Reaction. Application to the Synthesis of Aryl Cinnamic Acids.

Cited by 2 publications

References 1 publication

Benzamide capped peptidomimetics as non-ATP competitive inhibitors of CDK2 using the REPLACE strategy

Benzamide capped peptidomimetics as non-ATP competitive inhibitors of CDK2 using the REPLACE strategy

Biomodifications of resveratrol by Phanerochaete chrysosporium

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