27506-79-2Relevant academic research and scientific papers
Sustainable electrochemical decarboxylative acetoxylation of aminoacids in batch and continuous flow
K?ckinger, Manuel,Hanselmann, Paul,Roberge, Dominique M.,Geotti-Bianchini, Piero,Kappe, C. Oliver,Cantillo, David
supporting information, p. 2382 - 2390 (2021/04/12)
Introduction of acetoxy groups to organic molecules is important for the preparation of many active ingredients and synthetic intermediates. A commonly used and attractive strategy is the oxidative decarboxylation of aliphatic carboxylic acids, which entails the generation of a new C(sp3)-O bond. This reaction has been traditionally carried out using excess amounts of harmful lead(iv) acetate. A sustainable alternative to stoichiometric oxidants is the Hofer-Moest reaction, which relies on the 2-electron anodic oxidation of the carboxylic acid. However, examples showing electrochemical acetoxylation of amino acids are scarce. Herein we present a general and scalable procedure for the anodic decarboxylative acetoxylation of amino acids in batch and continuous flow mode. The procedure has been applied to the derivatization of several natural and synthetic amino acids, including key intermediates for the synthesis of active pharmaceutical ingredients. Good to excellent yields were obtained in all cases. Transfer of the process from batch to a continuous flow cell signficantly increased the reaction throughput and space-time yield, with excellent product yields obtained even in a single-pass. The sustainability of the electrochemical protocol has been examined by evaluating its green metrics. Comparison with the conventional method demonstrates that an electrochemical approach has a significant positive effect on the greenness of the process.
Structure-activity relationships of 3-substituted-5,5-diphenylhydantoins as potential antiproliferative and antimicrobial agents
Trisovic, Nemanja,Bozic, Bojan,Obradovic, Ana,Stefanovic, Olgica,Markovic, Snezana,Comic, Ljiljana,Bozic, Biljana,Uscumlic, Gordana
scheme or table, p. 1597 - 1606 (2012/05/07)
A series of twelve 3-substituted-5,5-diphenylhydantoins was synthesized, including some whose anticonvulsant activities have already been reported in the literature. Their antiproliferative activities against HCT-116 human colon carcinoma cells were evalu
Solvent effects on the structure-activity relationship of pharmacological active 3-substituted-5,5-diphenylhydantoins
Banjac, Nebojsa,Uscumlic, Gordana,Valentic, Natasa,Mijin, Dusan
, p. 869 - 878 (2008/02/08)
Absorption spectra of eight 3-substituted-5,5-diphenylhydantoins have been recorded in fourteen solvents in the range 200-400 nm. The effect of solvent dipolarity/polarizability and solvent/solute hydrogen bonding interactions are analyzed by means of the
Phenytoin prodrugs III: Water-soluble prodrugs for oral and/or parenteral use
Varia,Schuller,Sloan,Stella
, p. 1068 - 1073 (2007/10/02)
Various bioreversible derivatives of phenytoin, a poorly water soluble and erratically absorbed drug after both oral and parenteral dosing, were synthesized. Initial evaluation of these expected prodrugs, i.e., their aqueous solubility, cleavage in the presence of various animal tissues, and anticonvulsant activity in mice, confirmed that a number of the derivatives did indeed behave as prodrugs. The more promising prodrugs were the disodium phosphate ester and various amino groups containing acyl esters of 3-(hydroxymethyl)-5,5-diphenylhydantoin.
Low-melting phenytoin prodrugs as alternative oral delivery modes for phenytoin: A model for other high-melting sparingly water-soluble drugs
Yamaoka,Roberts,Stella
, p. 400 - 405 (2007/10/02)
Phenytoin is a high-melting, weakly acidic, and sparingly water-soluble drug. Because of these physicochemical properties, phenytoin is subject to erratic bioavailability in a variety of dosage forms both in its acidic as well as sodium salt forms. A homo
