5857-27-2Relevant 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.
Synthesis of 7a-substituted Hajos-Wiechert ketone analogues
Kennedy, Jason W. J.,Vietrich, Sophia,Weinmann, Hilmar,Brittain, Dominic E. A.
, p. 5151 - 5154 (2008/09/21)
(Chemical Equation Presented) A general and efficient route to 2-substituted 1,3-cyclopentadiones 3 has been developed. This operationally simple, two-step procedure is amenable to multigram scale preparations of these useful synthetic intermediates. These compounds are then transformed to previously unknown, higher analogues of the Hajos-Parrish-Eder-Sauer-Wiechert ketone (enone 1, R = Me) following an enantioselective Robinson annulation.
Novel Cycloalkenone Acetic and Oxy-acetic Acids as Aldose Reductase Inhibitors
Malamas, Michael S.,Hohman, Thomas C.
, p. 245 - 254 (2007/10/03)
Two new series of naphthalene substituted cycloalkenone acetic and oxy-acetic acids (1a, 1b), based on the known aldose reductase (AR) inhibitors tolrestat (2) and ICI-105,552 (3) were prepared and evaluated for their ability to inhibit partially purified
CHEMIOSELECTIVITY IN THE PRESENCE OF SURFACTANTS. I. C- vs. O-ALKYLATION IN β-DICARBONYL COMPOUNDS
Bassetti, Mauro,Cerichelli, Giorgio,Floris, Barbara
, p. 583 - 586 (2007/10/02)
A number of β-dicarbonyl compounds (2,4-pentanedione, 5,5-dimethyl-1,3-cyclohexanedione, 1,3-cyclopentanedione, ethyl 3-oxobutanoate, and diethyl propanedioate) reacted with benzyl bromide in basic aqueous solutions of hexadecyltrimethylammonium bromide at room temperature.The presence of the cationic surfactant directed the reaction toward the carbon nucleophilic site, with high chemioselectivity.C-Dialkylated species were generally predominant, due to the increased lipophilicity of the monoalkylated species, with respect to the reagent.No hydrolysis of benzyl bromide was observed in the presence of the surfactant.
