Structure Property Relationships of Carboxylic Acid Isosteres
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 physicoche...
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| Published in | Journal of medicinal chemistry Vol. 59; no. 7; pp. 3183 - 3203 |
|---|---|
| Main Authors | , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
14.04.2016
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0022-2623 1520-4804 1520-4804 |
| DOI | 10.1021/acs.jmedchem.5b01963 |
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| Abstract | 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. |
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| AbstractList | 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. 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.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. 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. |
| Author | Gay, Bryant Tran, Van Smith, Amos B Huryn, Donna M Lassalas, Pierrik Vijayendran, Krishna G Brunden, Kurt R Lasfargeas, Caroline James, Michael J Ballatore, Carlo Kozlowski, Marisa C Thomas, Craig J |
| AuthorAffiliation | National Center for Advancing Translational Sciences Center for Neurodegenerative Disease Research National Institutes of Health Department of Chemistry, School of Arts and Sciences University of Pennsylvania |
| AuthorAffiliation_xml | – name: University of Pennsylvania – name: Department of Chemistry, School of Arts and Sciences – name: National Institutes of Health – name: National Center for Advancing Translational Sciences – name: Center for Neurodegenerative Disease Research |
| Author_xml | – sequence: 1 givenname: Pierrik surname: Lassalas fullname: Lassalas, Pierrik – sequence: 2 givenname: Bryant surname: Gay fullname: Gay, Bryant – sequence: 3 givenname: Caroline surname: Lasfargeas fullname: Lasfargeas, Caroline – sequence: 4 givenname: Michael J surname: James fullname: James, Michael J – sequence: 5 givenname: Van surname: Tran fullname: Tran, Van – sequence: 6 givenname: Krishna G surname: Vijayendran fullname: Vijayendran, Krishna G – sequence: 7 givenname: Kurt R surname: Brunden fullname: Brunden, Kurt R – sequence: 8 givenname: Marisa C surname: Kozlowski fullname: Kozlowski, Marisa C – sequence: 9 givenname: Craig J surname: Thomas fullname: Thomas, Craig J – sequence: 10 givenname: Amos B surname: Smith fullname: Smith, Amos B – sequence: 11 givenname: Donna M surname: Huryn fullname: Huryn, Donna M email: huryn@sas.upenn.edu – sequence: 12 givenname: Carlo surname: Ballatore fullname: Ballatore, Carlo email: bcarlo@sas.upenn.edu |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26967507$$D View this record in MEDLINE/PubMed |
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| Snippet | The replacement of a carboxylic acid with a surrogate structure, or (bio)-isostere, is a classical strategy in medicinal chemistry. The general underlying... The replacement of a carboxylic acid with a surrogate structure, or (bio)-isostere, is a classical strategy in medicinal chemistry. The general underlying... |
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| SubjectTerms | Carboxylic Acids - chemistry Chemistry, Medicinal Chemistry, Pharmaceutical Life Sciences & Biomedicine Mass Spectrometry Models, Molecular Molecular Structure Pharmacology & Pharmacy Phenylpropionates - chemistry Plasma - chemistry Plasma - drug effects Science & Technology Structure-Activity Relationship |
| Title | Structure Property Relationships of Carboxylic Acid Isosteres |
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