264609-15-6Relevant academic research and scientific papers
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)
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.
Cu2O spheres as an efficient source of catalytic Cu(I) species for performing azide-alkyne click reactions
Rodrigues, Thenner S.,da Silva, Anderson G.M.,de Oliveira, Lucas C.,da Silva, Adalberto M.,Teixeira, Róbson R.,Camargo, Pedro H.C.
supporting information, p. 590 - 595 (2017/01/16)
We report herein the high yield synthesis of Cu2O spheres displaying well-defined shapes and monodisperse sizes that could be employed as the source of highly catalytic active Cu(I) species towards click reactions between several of alkynes and azides to produce a variety of 1,2,3-triazoles under ligand-free and ambient conditions (in an open reactor). The utilization of Cu2O spheres enabled superior performance as compared to a conventional protocol in which CuSO4is employed in combination with sodium ascorbate as the catalyst system. In addition, the compounds were obtained in synthetically useful yields, and seven of them have not been previously reported. We believe the results reported herein shed new insights into the optimization of activity and versatility of click reactions towards the synthesis of target molecules in environmentally friendly conditions.
NHC-catalyzed C-O or C-N bond formation: Efficient approaches to α,β-unsaturated esters and amides
Zhang, Bo,Feng, Peng,Cui, Yuxin,Jiao, Ning
supporting information; experimental part, p. 7280 - 7282 (2012/07/28)
Simple and efficient NHC-catalyzed transformations of bromoenal or α,β-dibromoenal into α,β-unsaturated esters or amides with high stereoselectivity through C-O or C-N bond formation have been demonstrated. The NHC-catalyzed processes occur under mild con
