Green synthesis of novel chalcone and coumarin derivatives via Suzuki coupling reaction

Vieira, Lucas Campos Curcino; Paixão, Márcio W.; Corrêa, Arlene G.

doi:10.1016/j.tetlet.2012.03.079

Cited by 47 publications

(22 citation statements)

References 48 publications

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“…Owing to the value of these molecules, a search for new and more convenient methods of preparation is desirable, mainly if the novel offered procedure diminished pollution; in other words, with proper green approach, the adoption of novel cleaner methods must be an urgent priority. Some efforts, with occurrence in the Green Chemistry Protocol, have been explored to prepare coumarins derivatives, many of them using green approaches, for example, zeolites [23], clays [22], cation exchange resins [24], solventless [25] and solidphase [26] conditions, reflux in water [18], microwave irradiation [19], oxidative cyclocarbonylation [27], using mixtures of 2 Journal of Chemistry PEG400/H 2 O or PEG400/EtOH as solvents [28], ultrasound [29], and room temperature [30]. However, many of these procedures involve long time reactions and the presence of a solvent or catalyst or both.…”

Section: Introductionmentioning

confidence: 99%

Uncatalysed Production of Coumarin-3-carboxylic Acids: A Green Approach

Martínez

Sanchez

Pérez

et al. 2016

Journal of Chemistry

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A green contribution in short reaction times with moderate yields to produce coumarin-3-carboxylic acids is offered. Five different modes to activate the reactions (microwave, near-infrared, mechanical milling, and ultrasound) were compared with mantle heating in the presence or absence of ethanol, a green solvent. Near-infrared and microwave irradiations deliver the best yields in contrast to ultrasound and mechanical milling; moreover, these four processes offered shorter reaction times in comparison with the conventional mantle heating method. It is also important to highlight that the obtained molecules were produced without the requirement of a catalyst and two nonconventional energies forms are presented as new processes.

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Section: Introductionmentioning

confidence: 99%

Uncatalysed Production of Coumarin-3-carboxylic Acids: A Green Approach

Martínez

Sanchez

Pérez

et al. 2016

Journal of Chemistry

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“…2-Mercaptobenzimidazole 98%, 2-mercaptobenzoxazole 99%, 6-mercaptopurine ≥ 99.5%, 2-mercapto-5-methylbenzimidazole 99% and resorcinol sulfide 98% were purchased from Acros Organics (Geel, Belgium). The coumarins LSPN214 and LSPN234 were prepared as previously described, 33 and, for coumarins LSPN223, LSPN224 and LSPN272, see Supplementary Information (SI) section. Gemifloxacin (lot: QUB10006) was donated by Ache (São Paulo-SP, Brazil).…”

Section: Methodsmentioning

confidence: 99%

Direct Assay to Evaluate Phosphoenolpyruvate Carboxykinase Activity

Amaral

Correa

Corrêa

et al. 2019

J. Braz. Chem. Soc.

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Phosphoenolpyruvate carboxykinase (PEPCK) is a ubiquitous enzyme found in all known groups of organisms, acting in the reversible conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP) in the presence of divalent metal ion, and dependent of adenosine 5'-triphosphate (ATP) or guanosine-5'-triphosphate (GTP). PEPCK is an important enzyme in the metabolism of some organisms, such as Trypanosoma cruzi, being suggested as a potential drug target to treat Chagas' disease. Its catalytic activity is, classically, measured by coupled assays. Herein, a direct assay by liquid chromatography-tandem mass spectrometry (LC-MS/MS) capable of quantifying PEP, in co-elution with OAA by the differentiation obtained by the mass spectra, is reported. The developed assay was used throughout the purification protocol in order to measure the activity of PEPCK of T. cruzi, which was expressed in Escherichia coli. The purified enzyme was kinetically characterized by the developed method with Michaelis-Menten constant (K Mapp) values of 96 ± 4 and 275 ± 18 μmol L-1 to OAA and ATP as substrates, respectively. The developed assay was also used for ligand screening and proved to be able to identify very low inhibitions for small molecules (50 μmol L-1).

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“…As reações foram realizadas em condições de química verde, usando irradiação de micro-ondas (MO) e polietilinoglicol como solvente, e as cumarinas aril-substituídas (10) tiveram sua atividade avaliada na enzima acetilcolinesterase imobilizada, apresentando atividade inibitória (Esquema 2). 29,30 Recentemente, Cogo e colaboradores sintetizaram uma coleção de quinoxalinas empregando a variação de blocos sintéticos e grupos funcionais para a diversificação estrutural. Neste trabalho, alguns derivados quinoxalínicos contendo os grupos funcionais amino e sulfonas ou sulfóxidos, foram identificados como novos agentes promissores no tratamento da doença de chagas e leishmaniose, com destaque para o composto 11 (Esquema 3).…”

Section: Síntese Orientada Pela Diversidade Estruturalunclassified

Synthetic Strategies in Drug Discovery: Employng Diversity-Oriented Synthesis

Sangi¹

2016

Química Nova

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publicado na web em 25/05/2016 SYNTHETIC STRATEGIES IN DRUG DISCOVERY: EMPLOYNG DIVERSITY-ORIENTED SYNTHESIS. Drug discovery often involves screening synthetic small molecules for their ability to bind to a macromolecular target. Target-Oriented Synthesis of a specific compound or a focused library can be planned combining retrosynthetic analysis and rational drug design. Biologically active molecules also can be identified through the unfocused screening of compound libraries. Diversity-Oriented Synthesis (DOS) emerges as an excellent strategy that leads to a library of structurally complex and diverse small molecules, covering a larger chemical space and increasing the probability of identifying modulators.Keywords: target oriented synthesis; diversity oriented synthesis; drug discovery. INTRODUÇÃOAntes do desenvolvimento da síntese orgânica, a obtenção de substâncias orgânicas para os seus diversos fins, inclusive terapêuti-cos, era feita por processos de fermentação ou isolamento de fontes naturais. Devido a sua ampla diversidade estrutural e funcional, muitos compostos de origem natural são usados no tratamento de diversos males e desordens biológicas.Por anos, a maioria dos fármacos disponíveis no mercado eram produtos naturais ou mesmo análogos inspirados neles, alguns obtidos por modificação estrutural outros por síntese total, quando a fonte natural não supria a demanda. 1,2Os produtos naturais bioativos geralmente são isolados em baixas quantidades, e muitas vezes apresentam alta complexidade estrutural, contendo vários centros estereogênicos. A complexidade destes compostos dificulta muito a sua obtenção através de métodos sintéticos rápidos e a baixa disponibilidade inviabiliza o seu emprego em High-Throughput Screening (HTS).Portanto, a busca por lucros mais rápidos por parte das indústrias farmacêuticas aliada ao grande desenvolvimento dos métodos de síntese orgânica fez com que os produtos naturais deixassem de ser a maior fonte de novos fármacos, sendo substituídos por compostos sintéticos. 1A identificação das funções biológicas, o isolamento e determinação estrutural de muitas macromoléculas e de seus ligantes naturais têm permitido o planejamento racional de moduladores destes novos alvos macromoleculares. Desta forma, a síntese de coleções focadas empregando a química combinatória emergiu como uma das principais ferramentas na busca por novos fármacos.Nas últimas décadas a área de síntese orgânica passou por uma grande evolução 3 . O número e a complexidade dos novos compostos sintetizados aumentaram drasticamente, e dentre estes novos compostos pode-se incluir um grande número de fármacos e candidatos, além de muitos reagentes usados para explorar processos biológicos de várias formas.Atualmente, a síntese de compostos orgânicos constitui uma importante parte no processo de descoberta e desenvolvimento de novos fármacos. Na busca por um fármaco que tenha como alvo uma macromolécula biológica, anteriormente selecionada, é comum fazer uso da estratégia de síntese orientada pelo alvo, seja com ...

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Green synthesis of novel chalcone and coumarin derivatives via Suzuki coupling reaction

Cited by 47 publications

References 48 publications

Uncatalysed Production of Coumarin-3-carboxylic Acids: A Green Approach

Uncatalysed Production of Coumarin-3-carboxylic Acids: A Green Approach

Direct Assay to Evaluate Phosphoenolpyruvate Carboxykinase Activity

Synthetic Strategies in Drug Discovery: Employng Diversity-Oriented Synthesis

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