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.
Application of Ugi three component reaction for the synthesis of quinapril hydrochloride
Borase, Bhushan B.,Godbole, Himanshu M.,Singh, Girij P.,Upadhyay, Pritesh R.,Trivedi, Anurag,Bhat, Varadaraj,Shenoy, Gautham G.
supporting information, p. 48 - 55 (2019/11/19)
A novel, efficient and concise synthesis of chirally pure quinapril hydrochloride is described. The key step is the formation of α-amino amide backbone in one step using Ugi three component reaction. This method allows short access to α-amino amide chain which is a part of many drugs used for treatment of high blood pressure. A large molecular library can be synthesized by changing the components in Ugi reaction.
Biomimetic synthesis of galantamine: Via laccase/TEMPO mediated oxidative coupling
Baratto, Maria Camilla,Bizzarri, Bruno Mattia,Botta, Lorenzo,Pogni, Rebecca,Saladino, Raffaele,Zippilli, Claudio
, p. 10897 - 10903 (2020/03/27)
Laccase-mediated intramolecular oxidative radical coupling of N-formyl-2-bromo-O-methylnorbelladine afforded a novel and isolable spirocyclohexadienonic intermediate of galantamine. High yield and conversion of substrate were obtained in the presence of the redox mediator 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). This laccase procedure, with an overall yield of 34%, represents a scalable and environmentally friendly alternative to previously reported syntheses of galantamine based on the use of potassium ferricyanide as an unspecific radical coupling reagent.
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.
Total synthesis of cannabisin F
Xia, Ya-Mu,Xia, Jun,Chai, Chen
, p. 384 - 391 (2014/01/06)
A practical eight-step synthesis of lignanamide cannabisin F starting from vanillin is reported for the first time. This synthetic strategy applies the aldol reaction followed by the Wittig reaction to afford the key 8-O-4′-neolignan intermediate diacid. The diacid was condensed with N,O-protected tyramine giving, after deprotection, cannabisin F.
Tandem Ugi MCR/mitsunobu cyclization as a short, protecting-group-free route to benzoxazinones with four diversity points
Banfi, Luca,Basso, Andrea,Giardini, Lorenzo,Riva, Renata,Rocca, Valeria,Guanti, Giuseppe
experimental part, p. 100 - 109 (2011/03/21)
A tandem Ugi/Mitsunobu protocol, starting from o-aminophenols, α-hydroxy acids, amines and aldehydes gives benzo[b][1,4]oxazin-3-ones of general formula 1 in two high-yielding steps, with the introduction of up to four diversity inputs. The mildness of the methodology allows the stereospecific synthesis of enantiomerically pure products as well as the introduction of additional functional groups. The overall procedure can also be carried out in a one-pot manner. A tandem Ugi/Mitsunobu protocol, starting from o-aminophenols and α-hydroxy acids, gives benzo[b][1,4]oxazin-3-ones, with the introduction of up to four diversity inputs, in two high-yielding steps. The procedure may be carried out in a one-pot fashion and has a very broad scope, also allowing the synthesis of enantiomerically pure products.
One-step synthesis of natural product-inspired biaryl ether-cyclopeptoid macrocycles by double ugi multiple-component reactions of bifunctional building blocks
Michalik, Dirk,Schaks, Angela,Wessjohann, Ludger A.
, p. 149 - 157 (2007/10/03)
Isonitrile-functionalized biaryl ethers can serve as key building blocks for the highly efficient one-step production of natural product inspired-macrocycles, with six or even twelve new bonds and rings with up to 50 members being formed in total yields o
Antiplasmodial metabolites isolated from the marine octocoral Muricea austera
Gutierrez, Marcelino,Capson, Todd L.,Guzman, Hector M.,Gonzalez, Jose,Ortega-Barria, Eduardo,Quinoa, Emilio,Riguera, Ricardo
, p. 1379 - 1383 (2008/09/20)
Bioassay-guided fractionation of the MeOH extract from the octocoral Muricea austera collected in the Pacific coast of Panama led to the isolation of eight compounds, including three tyramine derivatives (1-3), two steroidal pregnane glycosides (4, 5), and three sesquiterpenoids (6-8). Compounds 2-5 are new natural products, and their structures were determined on the basis of their spectroscopic data (HRMS, 1D and 2D NMR, and CD studies). The antiprotozoal activities of the natural compounds 1-8 as well as those of a series of synthetic glycosides (11-22) and tyramine derivatives (23-35) were evaluated in vitro against a drug-resistant Plasmodium falciparum and intracellular form of Trypanosoma cruzi.
