Stereoselective synthesis and antitumoral activity of Z-enyne pseudoglycosides

Dantas, Claudio R.; Freitas, Jucleiton José Rufino de; Barbosa, Queila P. S.; Militão, Gardênia Carmen Gadelha; Silva, Thiago D S; Silva, Teresinha G. da; Paulino, Antonio A. S.; Freitas, Juliano Carlo Rufino; Oliveira, Roberta A.; Menezes, Paulo H.

doi:10.1039/c6ob00945j

Cited by 8 publications

(3 citation statements)

References 37 publications

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“…Devido essas e outras aplicações dos O-glicosídeos, nosso grupo de pesquisa vem dedicando esforços, nos últimos anos, no desenvolvimento de novas estratégias sintéticas e na avalição biológica desses compostos [10,27,28,29]. Contudo, o assinalamento inequívoco desses compostos continua sendo um desafio, uma vez que suas estruturas são complexas e bem diversificadas [16].…”

Section: Figura 1: Exemplos De Produtos Naturais (Glicosídeos) Versus Suas Atividades Biológicasunclassified

Assinalamento Completo e Avaliação do Perfil Farmacocinético e Toxicológico do 3-butin-1-il 4,6-di-O-acetil-2,3-didesoxi-α-D-eritro-hex-2-enopiranosídeo

et al. 2020

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O desenvolvimento de novos fármacos que exibam baixa toxicidade é de grande importância, uma vez que inúmeros candidatos são descartados devido a não atenderem a esse pré-requisito. Neste sentido, o trabalho descreve o assinalamento completo dos núcleos de hidrogênio e carbono, bem como a avaliação do perfil farmacocinético e toxicológico do 3-butin-1-il 4,6-di-O-acetil-2,3-didesoxi-α-D-eritro-hex-2-enopiranosídeo. O assinalamento completo, o estudo toxicológico frente às larvas da Artemia salina e a estudo farmacocinético in silico para este composto são descritos pela primeira vez. Este composto foi obtido com ótimo rendimento e o experimento de NOESY permitiu confirmar a estrutura do anômero majoritário da reação de glicosilação. A avaliação do perfil farmacocinético e toxicológico confirmou que este composto apresenta ótima biodisponibilidade e absorção pela via oral, além de baixa toxicidade.

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Section: Figura 1: Exemplos De Produtos Naturais (Glicosídeos) Versus Suas Atividades Biológicasunclassified

Assinalamento Completo e Avaliação do Perfil Farmacocinético e Toxicológico do 3-butin-1-il 4,6-di-O-acetil-2,3-didesoxi-α-D-eritro-hex-2-enopiranosídeo

et al. 2020

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“…Other important contributions involve new protocols for synthetic useful transformations (Ahmad et al 2013) and the application of hypervalent iodine based Figure 62 -Addition of arylzinc reagents to aldehydes (a) and synthesis of glycosyl amides using in situ generated lithium selenocarboxylates (b) reported by Lüdtke (Martins and Lüdtke 2014, Martins et al 2017. Figure 63 -Addition of (Z)-1,3-enynes pseudoglycosides reported by Menezes (Dantas et al 2016). RONALDO A. PILLI and FRANCISCO F. DE ASSIS methodologies in the synthesis of pharmaceutical ingredients (Silva Jr et al 2007).…”

Section: Examples Of Large-scale Complex Synthesesmentioning

confidence: 99%

Organic Synthesis: New Vistas in the Brazilian Landscape

Pilli

Assis

2018

An. Acad. Bras. Ciênc.

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In this overview, we present our analysis of the future of organic synthesis in Brazil, a highly innovative and strategic area of research which underpins our social and economical progress. Several different topics (automation, catalysis, green chemistry, scalability, methodological studies and total syntheses) were considered to hold promise for the future advance of chemical sciences in Brazil. In order to put it in perspective, contributions from Brazilian laboratories were selected by the citations received and importance for the field and were benchmarked against some of the most important results disclosed by authors worldwide. The picture that emerged reveals a thriving area of research, with new generations of well-trained and productive chemists engaged particularly in the areas of green chemistry and catalysis. In order to fulfill the promise of delivering more efficient and sustainable processes, an integration of the academic and industrial research agendas is to be expected. On the other hand, academic research in automation of chemical processes, a well established topic of investigation in industrial settings, has just recently began in Brazil and more academic laboratories are lining up to contribute. All these areas of research are expected to enable the future development of the almost unchartered field of scalability.

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“…Additionally, 6c has anticancer activity with an IC 50 of 6.5 μg/mL in an HL-60 (human acute promyelocytic leukemia) tumor cell line (Figure ). 1,3-Enynes are used as synthetic intermediates for constructing heterocycles including highly substituted aryl rings, thiophenes, pyrroles, and furans . Access to 1,3-enynes can be challenging, as E / Z isomers can be generated.…”

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confidence: 99%

Regio- and Stereoselective Copper-Catalyzed Borylation–Protodeboronation of 1,3-Diynes: Access to (Z)-1,3-Enynes

2023

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A facile method to access (Z)-1,3-enynes is realized via sequential copper-catalyzed regio-and stereoselective borylation−protodeboronation of 1,3-diynes. Pinacolborane, copper(II) acetate, and Xantphos as the ligand efficiently install hydrogen and Bpin in a cis fashion, which is followed by rapid hydrolysis with water. The reaction has wide substrate scope and occurs in a chemoselective fashion.

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Stereoselective synthesis and antitumoral activity of Z-enyne pseudoglycosides

Cited by 8 publications

References 37 publications

Assinalamento Completo e Avaliação do Perfil Farmacocinético e Toxicológico do 3-butin-1-il 4,6-di-O-acetil-2,3-didesoxi-α-D-eritro-hex-2-enopiranosídeo

Assinalamento Completo e Avaliação do Perfil Farmacocinético e Toxicológico do 3-butin-1-il 4,6-di-O-acetil-2,3-didesoxi-α-D-eritro-hex-2-enopiranosídeo

Organic Synthesis: New Vistas in the Brazilian Landscape

Regio- and Stereoselective Copper-Catalyzed Borylation–Protodeboronation of 1,3-Diynes: Access to (Z)-1,3-Enynes

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