340258-61-9Relevant academic research and scientific papers
An alternative way to analogues of avenanthramides and their antiradical activity
Mierina, Inese,Stikute, Agnese,Mishnev, Anatoly,Jure, Mara
, p. 85 - 101 (2018/11/23)
Abstract: The paper is devoted to the synthesis of arylidene malonic acid monoanilides and cinnamoyl anilines by condensation of malonic acid monoanilides with aromatic aldehydes. The presented synthetic route applies simple, cheap, and commercially available aromatic aldehydes and amines, thus overcoming traditional schemes, which involve derivatives of hydroxycinnamic acids. Besides, a mild and effective pyridine-mediated decarboxylation of carboxylic group at Csp2 in arylidene malonic acid monoanilides leading to cinnamoyl anilines is presented. The structures of obtained selected arylidene derivatives were approved additionally by X-ray analysis. The antiradical properties (2,2-diphenyl-1-picrylhydrazyl and galvinoxyl tests) and structure–activity relationships of the synthesized compounds were studied. Graphical abstract: [Figure not available: see fulltext.].
Substituted Hantzsch Esters as Versatile Radical Reservoirs in Photoredox Reactions
Gu, Fangjun,Huang, Wenhao,Liu, Xu,Chen, Wenxin,Cheng, Xu
supporting information, p. 925 - 931 (2018/01/04)
Substituted Hantzsch esters can act as radical reservoirs in photoredox reactions, steadily releasing a carbon radical and a hydrogen atom radical in the absence of an additional electron acceptor. We propose that radical release by substituted Hantzsch esters occurs via a mechanism involving an internal redox cycle. Cinnamidecinnamides, styrenes, α,β-unsaturated acids, and diarylethenes could be alkylated smoothly with these reagents. (Figure presented.).
Copper-catalyzed direct transformation of secondary allylic and benzylic alcohols into azides and amides: An efficient utility of azide as a nitrogen source
Rokade, Balaji V.,Gadde, Karthik,Prabhu, Kandikere Ramaiah
, p. 2706 - 2717 (2015/04/27)
A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation of ω-halo azides and the azidation of allylic alcohols in the presence of a benzyl alcohol moiety. In addition, this strategy provides an opportunity to synthesize azides that can serve as precursors to β-amino acids. A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has also been adapted to the preparation of azides directly from their corresponding alcohols.
Identification and specificity studies of small-molecule ligands for SH3 protein domains
Inglis, Steven R.,Stojkoski, Cvetan,Branson, Kim M.,Cawthray, Jacquie F.,Fritz, Daniel,Wiadrowski, Emma,Pyke, Simon M.,Booker, Grant W.
, p. 5405 - 5417 (2007/10/03)
The Src Homology 3 (SH3) domains are small protein-protein interaction domains that bind proline-rich sequences and mediate a wide range of cell-signaling and other important biological processes. Since deregulated signaling pathways form the basis of many human diseases, the SH3 domains have been attractive targets for novel therapeutics. High-affinity ligands for SH3 domains have been designed; however, these have all been peptide-based and no examples of entirely nonpeptide SH3 ligands have previously been reported. Using the mouse Tec Kinase SH3 domain as a model system for structure-based ligand design, we have identified several simple heterocyclic compounds that selectively bind to the Tec SH3 domain. Using a combination of nuclear magnetic resonance chemical shift perturbation, structure-activity relationships, and site-directed mutagenesis, the binding of these compounds at the proline-rich peptide-binding site has been characterized. The most potent of these, 2-aminoquinoline, bound with Kd = 125 μM and was able to compete for binding with a proline-rich peptide. Synthesis of 6-substitued-2- aminoquinolines resulted in ligands with up to 6-fold improved affinity over 2-aminoquinoline and enhanced specificity for the Tec SH3 domain. Therefore, 2-aminoquinolines may potentially be useful for the development of high affinity small molecule ligands for SH3 domains.
