Synthesis of coumarin-3-carboxylic esters via FeCl3-catalyzed multicomponent reaction of salicylaldehydes, Meldrum's acid and alcohols

He, Xinwei; Shang, Yongjia; Zhou, Yao; Yu, Zhiyu; Han, Guang; Jin, Wenjing; Chen, Jiaojiao

doi:10.1016/j.tet.2014.12.042

Cited by 64 publications

(28 citation statements)

References 41 publications

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“…Coumarins are very attractive targets for combinatorial library synthesis due to their wide range of valuable biological activities (He et al 2015). They were first synthesized in 1868, and it was used in the pharmaceutical industry as a precursor in the synthesis of a number of anticoagulant pharmaceuticals.…”

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 secondary metabolites have many bioactivities such as anti‐acetylcholinesterase, anti‐bacterial, anti‐cancer, anti‐coagulant, anti‐fungal, anthelmintic, anti‐inflammatory, anti‐HIV, anti‐microbial, anti‐oxidant and anti‐viral activities ,,,. Coumarins are utilized in wide range of applications, not only as pharmaceuticals but also as cosmetics, fragrances, agrochemicals, insecticides, in food industry and in color technology ,. Additionally, coumarins have been used in pharmaceutical industry as precursors in the synthesis of anticoagulant agents since 1868 .…”

Section: Resultsmentioning

confidence: 99%

“…[41,42,24,43] Coumarins are utilized in wide range of applications, not only as pharmaceuticals but also as cosmetics, fragrances, agrochemicals, insecticides, in food industry and in color technol-ogy. [24,44] Additionally, coumarins have been used in pharmaceutical industry as precursors in the synthesis of anticoagulant agents since 1868. [24] In recent years, the production of chemicals by microbial conversion is becoming an important component of industrial biotechnology.…”

Section: Resultsmentioning

confidence: 99%

Epigenetic Manipulation Induces the Production of Coumarin‐Type Secondary Metabolite from Arthrobotrys foliicola

Hsueh

et al. 2019

Israel Journal of Chemistry

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Pursuing epigenetic manipulation approach in fungi led to the isolation of an unusual coumarin metabolite from fungi. An addition of the histone deacetylase inhibitor, suberohydroxamic acid (SBHA), to the culture medium of Arthrobotrys foliicola induced production of the coumarin‐type secondary metabolite represented by a single intensive peak in the HPLC profile of the ethyl acetate extract. The compound which was identified as 4‐ethyl‐7‐hydroxy‐8‐methyl‐2H‐chromen‐2‐one (1) was isolated from nature for the first time. Moreover, the investigation on the remaining part of the HPLC profile led to the separation of 6‐ethyl‐2,4‐dihydroxy‐3‐methylbenzaldehyde (2) and ten 2,5‐diketopiperazine compounds (3–12). The structures of isolates were deduced by their mass and NMR spectroscopic data. The coumarin‐type secondary metabolite (1) with peculiar smell induced by epigenetic stimulation is found for the first time in the Arthrobotrys species and the family Orbiliaceae. We evaluated 1 for the cytotoxic, anti‐inflammatory, anti‐allergic and nematocidal activities, however, it was found inactive.

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“…Ethyl 2-oxo-2H-chromene-3-carboxylate (5b) [13] White solid. Ethyl 7-methoxy-2-oxo-2H-chromene-3-carboxylate (5c) [14] Ethyl 6-methyl-2-oxo-2H-chromene-3-carboxylate (5d) [15] …”

Section: Methodsmentioning

confidence: 99%