144221-09-0Relevant articles and documents
Br?nsted Acid-Catalysed Allylic Amination of 1-(2-Aminoaryl)prop-2-en-1-ols to 1,2-Dihydroquinolines
Day, David Philip,Henry, Stuart Adam,Zhao, Yichao,Jin, Jianwen,Clarkson, Guy James,Chan, Philip Wai Hong
, p. 673 - 681 (2018)
A highly efficient synthetic method to prepare 1,2-dihydroquinolines that relies on trifluoromethanesulfonic acid (TfOH)-catalysed allylic amination of 1-(2-aminoaryl)prop-2-en-1-ols is described. Achieved at a catalyst loading of 0.01 mol-% under mild conditions at room temperature, the reaction was found to be robust, with a wide range of substitution patterns tolerated. The corresponding N-heterocyclic adducts were obtained in good to excellent yields of 45-93 %.
Synthesis and biological evaluation of 2′-Aminochalcone: A multi-target approach to find drug candidates to treat Alzheimer's disease
Almeida, Wanda P.,Antoniolli, Giorgio,Kawano, Daniel Fabio,Lancellotti, Marcelo,Sakata, Renata P.,Guimar?es Barbosa, Euzébio
, (2020/09/04)
Alzheimer's disease (AD) is a neurodegenerative process that compromises cognitive functions. The physiopathology of AD is multifactorial and is mainly supported by the cholinergic and amyloid hypotheses, which allows the identification the fundamental role of some markers, such as the enzymes acetylcholinesterase (AChE) and β-secretase (BACE-1), and the β-amyloid peptide (Aβ). In this work, we prepared a series of chalcones and 2′-aminochalcones, which were tested against AChE and BACE-1 enzymes and on the aggregation of Aβ. All compounds inhibited AChE activity with different potencies. We have found that the majority of chalcones having the amino group are able to inhibit BACE-1, which was not observed for chalcones without this group. The most active compound is the one derived from 2,3-dichlorobenzaldeyde, having an IC50 value of 2.71 μM. A molecular docking study supported this result, showing a good interaction of the amino group with aspartic acid residues of the catalytic diade of BACE-1. Thioflavin-T fluorescence emission is reduced in 30 – 40%, when Aβ42 is incubated in the presence of some chalcones under aggregation conditions. In vitro cytotoxicity and in silico prediction of pharmacokinetic properties were also conducted in this study.
Nazarov cyclization of 1,4-pentadien-3-ols: Preparation of cyclopenta[b]indoles and spiro[indene-1,4′-quinoline]s
Wang, Zhiming,Xu, Xingzhu,Gu, Zhanshou,Feng, Wei,Qian, Houjun,Li, Zhengyi,Sun, Xiaoqiang,Kwon, Ohyun
supporting information, p. 2811 - 2814 (2016/02/18)
The first Lewis acid-catalyzed intramolecular interrupted Nazarov cyclization of 1,4-pentadien-3-ols is described. Using FeBr3 as the catalyst, a series of new substituted cyclopenta[b]indoles was prepared - through a sequence of Nazarov cyclization, nucleophilic amination, and isomerization - with good yields and high diastereo- and regioselectivities. A similar catalytic process was also developed for the synthesis of structurally interesting spiro[indene-1,4′-quinoline]s.
