88517-80-0Relevant academic research and scientific papers
Structure Property Relationships of Carboxylic Acid Isosteres
Lassalas, Pierrik,Gay, Bryant,Lasfargeas, Caroline,James, Michael J.,Tran, Van,Vijayendran, Krishna G.,Brunden, Kurt R.,Kozlowski, Marisa C.,Thomas, Craig J.,Smith, Amos B.,Huryn, Donna M.,Ballatore, Carlo
, p. 3183 - 3203 (2016/05/19)
The replacement of a carboxylic acid with a surrogate structure, or (bio)-isostere, is a classical strategy in medicinal chemistry. The general underlying principle is that by maintaining the features of the carboxylic acid critical for biological activity, but appropriately modifying the physicochemical properties, improved analogs may result. In this context, a systematic assessment of the physicochemical properties of carboxylic acid isosteres would be desirable to enable more informed decisions of potential replacements to be used for analog design. Herein we report the structure-property relationships (SPR) of 35 phenylpropionic acid derivatives, in which the carboxylic acid moiety is replaced with a series of known isosteres. The data set generated provides an assessment of the relative impact on the physicochemical properties that these replacements may have compared to the carboxylic acid analog. As such, this study presents a framework for how to rationally apply isosteric replacements of the carboxylic acid functional group.
A short and elegant synthesis of (±)-streptopyrrolidine
Shaameri, Zurina,Ali, Sharifah Hidayah Sharif,Mohamat, Mohd Fazli,Yamin, Bohari M.,Hamzah, Ahmad Sazali
, p. 320 - 325 (2013/06/04)
A brief and efficient approach for the synthesis of (±)-5-benzyl-4- hydroxy-2-pyrrolidine () from phenylalanine racemate is described. The key step is the stereocontrolled reduction of the keto functionality of benzylated pyrrolidinone intermediate () via sodium borohydride in carboxylic acid medium furnishing both (R,R)- and (S,S)-configured diastereomers. The natural (R,R) enantiomer (), however, crystallized out from its racemic mixture. Structure of was confirmed by NMR, IR, elemental analyzer, and single crystal X-ray crystallographic techniques.
Acetylation of Pyrrolidine-2,4-diones: A Synthesis of 3-Acyltetramic Acids. X-Ray Molecular Structure of 3--5-isopropyl-1-methylpyrrolidine-2,4-dione
Jones, Raymond C. F.,Begley, Michael J.,Peterson, Graeme E.,Sumaria, Suresh
, p. 1959 - 1968 (2007/10/02)
Pyrrolidine-2,4-diones, prepared from the corresponding α-amino acid esters by condensation with ethoxycarbonylacetic acid, Dieckmann cyclisation, and hydrolysis-decarboxylation, are acylated at C-3 by the acid chlorides of saturated, unsaturated, and are
