An efficient methodology for the synthesis of 3-styryl coumarins

Martins, Sérgio; Branco, Paula S.; Pereira, António

doi:10.1590/s0103-50532012000400014

Cited by 18 publications

(15 citation statements)

References 13 publications

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“…They are used as technological potential in pharmaceutical, agrochemical, fragrance industries, food, cosmetic industry, and in color technology as optical brightening agents or laser dyes (Daru and Stirling 2011;Santos et al 2013;Venugopala et al 2013;Vekariya and Patel 2014). Coumarins constitute the largest class of fluorescent dyes (Martins et al 2012).…”

Section: Introductionmentioning

confidence: 99%

Fungi as a source of natural coumarins production

Costa

Tavares

Oliveira

2016

Appl Microbiol Biotechnol

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Natural coumarins and derivatives are compounds that occur naturally in several organisms (plant, bacteria, and fungi) consisting of fused benzene and α-pyrone rings. These compounds show high technological potential applications in agrochemical, food, pharmaceuticals, and cosmetics industries. Therefore, the need for bulk production of coumarins and the advancement of the chemical and pharmaceutical industries led to the development of synthetic coumarin. However, biotransformation process, synthetic bioengineering, metabolic engineering, and bioinformatics have proven effective in the production of natural products. Today, these biological systems are recognized as green chemistry innovation and business strategy. This review article aims to report the potential of fungi for synthesis of coumarin. These microorganisms are described as a source of natural products capable of synthesizing many bioactive metabolites. The features, classification, properties, and industrial applications of natural coumarins as well as new molecules obtained by basidiomycetes and ascomycetes fungi are reported in order to explore a topic not yet discussed in the scientific literature.

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Section: Introductionmentioning

confidence: 99%

Fungi as a source of natural coumarins production

Costa

Tavares

Oliveira

2016

Appl Microbiol Biotechnol

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“…These 3‐vinyl coumarins were used as a substrate for the synthesis of several 3‐styrylcoumarins by very simple and efficient palladium coupling reactions. Depending upon the substitution pattern, the compounds showed pronounced bathochromic shifts and hyperchromic effects 5a,b,d. The palladium‐catalysed insertion of 3‐bromocoumarin into a number of alkenes, cycloalkenes and alkynes was also reported by others 6.…”

Section: Methodsmentioning

confidence: 64%

“…We have been particularly interested in the extension of the π‐delocalised system of the coumarin chromophore at the 3‐position. Our approach involved 1) building of the 3‐vinyl coumarin ring from readily available substrates5d or 2) vinylation of 3‐bromocoumarin derivatives 5a,b. These 3‐vinyl coumarins were used as a substrate for the synthesis of several 3‐styrylcoumarins by very simple and efficient palladium coupling reactions.…”

Section: Methodsmentioning

confidence: 99%

A Family of Styrylcoumarins: Synthesis, Spectroscopic, Photophysical and Photochemical Properties

Avó¹,

Martins²,

Parola³

et al. 2013

ChemPlusChem

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“…Those properties include high fluorescent quantum yields and molar absorption coefficients, large Stokes shifts, and thermal and pH stabilities. The coumarin derivative chromophore (coumarin 392 STP ester) [24] possesses most of these properties. The chemical and photophysical properties of this coumarin derivative, its low cost, and simplicity of preparation makes it particularly suitable for labeling.…”

Section: Introductionmentioning

confidence: 99%

“…The chemical and photophysical properties of this coumarin derivative, its low cost, and simplicity of preparation makes it particularly suitable for labeling. Another advantage of this coumarin family of compounds is that their photophysical and spectroscopic properties can be easily designed to suit the intended application [24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Development of a Simple Method for Labeling and Identification of Protein Binders in Art

et al. 2019

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Easel paintings are assets with an important historic and cultural value. They usually possess a multi-tiered structure, composed of different layers some of which may present protein binders, making it important to identify these materials for restoration and conservation purposes. We propose the identification of different protein binders by a new fluorescent labeling method employing a coumarin based chromophore, C392STP (sodium(E/Z)-4-(4-(2-(6,7-dimethoxycoumarin-3-yl)vinyl)benzoyl)-2,3,5,6-tetrafluorobenzenesulfo-nate). The method was optimized using commercial proteins and was further tested on proteins extracted from hen’s egg yolk, white bovine milk, and rabbit skin glue. To model more realistic conditions, paint models of easel paintings were prepared. The paint models were made with hen’s egg yolk, white bovine milk, and rabbit skin glue, mixed with different pigments and submitted to artificial aging. Then the extracted proteins from the paint models were labeled with C392 which allowed a sensitive and selective identification by polyacrylamide gel electrophoresis (PAGE) of the different protein binders used. As a final test, three 19th century easel paintings, from the Italian painter Giorgio Marini, were analyzed. The results show the potential of the proposed method for the identification of protein binders present in easel paintings.

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An efficient methodology for the synthesis of 3-styryl coumarins

Cited by 18 publications

References 13 publications

Fungi as a source of natural coumarins production

Fungi as a source of natural coumarins production

A Family of Styrylcoumarins: Synthesis, Spectroscopic, Photophysical and Photochemical Properties

Development of a Simple Method for Labeling and Identification of Protein Binders in Art

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