13062-78-7Relevant articles and documents
Total synthesis of a lignanamide from Aptenia cordifolia
Xia, Yamu,Li, Chenchen,Zhang, Huaizheng,Lin, Jiao,Chai, Chen
, p. 535 - 538 (2015)
(E,E)-N,N-Dityramin-4,4'-dihydroxy-3,5'-dimethoxy-ss,3'-bicinnamamide, a lignanamide isolated from Aptenia cordifolia, was synthesised from vanillin and tyramine. The key 8-5'-neolignan intermediate diacid was formed efficiently using oxidative coupling of the ferulic acid derivatives and the ring-opening reaction of a dihydrobenzofuran.
Rapid Discovery of Aspartyl Protease Inhibitors Using an Anchoring Approach
ünver, M. Yagiz,Camacho, Carlos Jamie,D?mling, Alexander,Haupenthal, J?rg,Heine, Andreas,Hirsch, Anna K. H.,Jumde, Varsha R.,Klebe, Gerhard,Konstantinidou, Markella,Magari, Francesca,Sutanto, Fandi
supporting information, (2020/04/10)
Pharmacophore searches that include anchors, fragments contributing above average to receptor binding, combined with one-step syntheses are a powerful approach for the fast discovery of novel bioactive molecules. Here, we are presenting a pipeline for the rapid and efficient discovery of aspartyl protease inhibitors. First, we hypothesized that hydrazine could be a multi-valent warhead to interact with the active site Asp carboxylic acids. We incorporated the hydrazine anchor in a multicomponent reaction and created a large virtual library of hydrazine derivatives synthetically accessible in one-step. Next, we performed anchor-based pharmacophore screening of the libraries and resynthesized top-ranked compounds. The inhibitory potency of the molecules was finally assessed by an enzyme activity assay and the binding mode confirmed by several soaked crystal structures supporting the validity of the hypothesis and approach. The herein reported pipeline of tools will be of general value for the rapid generation of receptor binders beyond Asp proteases.
Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides
Claes, Laurens,Janssen, Michiel,De Vos, Dirk E.
, p. 4297 - 4306 (2019/08/26)
Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio-based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal-free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2-propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N-formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one-pot catalytic system.