91368-35-3Relevant articles and documents
Synthesis and 5-lipoxygenase inhibitory activity of new cinnamoyl and caffeoylclusters
Doiron, Jeremie,Boudreau, Luc H.,Picot, Nadia,Villebonet, Benoit,Surette, Marc E.,Touaibia, Mohamed
, p. 1118 - 1121 (2009)
Novel cinnamoyl and caffeoyl clusters were synthesized by multiple Cu(I)-catalyzed [1,3]-dipolar cycloadditions and their anti-5-lipoxygenase inhibitory activity was tested. Caffeoyl cluster showed an improved 5-lipoxygenase inhibitory activity compared t
Further investigation of harmicines as novel antiplasmodial agents: Synthesis, structure-activity relationship and insight into the mechanism of action
Marinovi?, Marina,Poje, Goran,Perkovi?, Ivana,Fontinha, Diana,Prudêncio, Miguel,Held, Jana,Pessanha de Carvalho, Lais,Tandari?, Tana,Vianello, Robert,Raji?, Zrinka
, (2021/07/19)
The rise of the resistance of the malaria parasite to the currently approved therapy urges the discovery and development of new efficient agents. Previously we have demonstrated that harmicines, hybrid compounds composed from β-carboline alkaloid harmine
Neighboring Carbonyl Group Assisted Oxyacetoxylation of Propargylic Carboxylates with Retention of Chirality under Metal Free Condition
Pradhan, Tapas R.,Mohapatra, Debendra K.
supporting information, p. 3605 - 3611 (2019/07/04)
A metal-free oxyacetoxylation method of primary, secondary and tertiary propargylic carboxylates with retention of chirality was presented. The reaction proceeds through the intramolecular nucleophilic attack of the neighboring carbonyl group on an alkynyliodonium intermediate. The process is general with broad substrate scope and is amenable for application to a variety of propargyl carboxylates including those obtained from natural products. Insight into the mechanistic pathway by isotopic labelling (using H2O18 and D2O) and controlled experiments confirmed. (Figure presented.).
Synthesis and antimetastatic activity evaluation of cinnamic acid derivatives containing 1,2,3-triazolic portions
Lima, Graziela Domingues de Almeida,Rodrigues, Michelle Peixoto,Mendes, Tiago Ant?nio de Oliveira,Moreira, Gabriela Alves,Siqueira, Raoni Pais,da Silva, Adalberto Manoel,Vaz, Boniek Gontijo,Fietto, Juliana Lopes Rangel,Bressan, Gustavo Costa,Machado-Neves, Mariana,Teixeira, Róbson Ricardo
, p. 1 - 9 (2018/08/01)
It is herein described the preparation and evaluation of antimetastatic activity of twenty-six cinnamic acid derivatives containing 1,2,3-triazolic portions. The compounds were prepared using as the key step the Copper(I)-catalyzed azide (A)-alkyne (A) cycloaddition (C) (CuAAC reaction), also known as click reaction, between alkynylated cinnamic acid derivatives and different benzyl azides. The reactions were carried in CH2Cl2/H2O (1:1 v/v) at room temperature, and the triazole derivatives were obtained in yields ranging from 73%–99%. Reaction times varied from 5 to 40 min. The identity of the synthesized compounds was confirmed by IR and NMR (1H and 13C) spectroscopic techniques. They were then submitted to in vitro bioassays to investigate how they act over metastatic behavior of murine melanoma. The most potent compound, namely 3-(1-benzyl-1H-1,2,3-triazol-4-yl)propyl cinnamate (9a), showed significant antimetastatic and antiproliferative activities against B16-F10 cells. In addition, gelatin zymography and molecular docking analyses pointed to the fact that this compound has potential to interact with matrix metalloproteinase 9 (MMP-9) and MMP-2, which are directly involved in melanoma progression. Therefore, these findings suggest that cinnamic acid derivatives containing 1,2,3-triazolic portions may have potential for development of novel candidates for controlling malignant metastatic melanoma.
