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Evaluation of the cyclopentane-1,2-dione as a Potential Bio-Isostere of the Carboxylic Acid Functional Group

Evaluation of the cyclopentane-1,2-dione as a Potential Bio-Isostere of the Carboxylic Acid Functional Group

Carlo Ballatore, Bryant Gay, Longchuan Huang, Katie Herbst Robinson, Michael J James, John Q Trojanowski, Virginia M-Y Lee, Kurt R Brunden, Amos B Smith 3rd

Bioorg Med Chem Lett. 2014 Sep 1;24(17):4171-5.

PMID: 25127105

Abstract:

Cycloalkylpolyones hold promise in drug design as carboxylic acid bio-isosteres. To investigate cyclopentane-1,2-diones as potential surrogates of the carboxylic acid functional group, the acidity, tautomerism, and geometry of hydrogen bonding of representative compounds were evaluated. Prototypic derivatives of the known thromboxane A2 prostanoid (TP) receptor antagonist, 3-(3-(2-((4-chlorophenyl)sulfonamido)-ethyl)phenyl)propanoic acid, in which the carboxylic acid moiety is replaced by the cyclopentane-1,2-dione unit, were synthesized and evaluated as TP receptor antagonists. Cyclopentane-1,2-dione derivative 9 was found to be a potent TP receptor antagonist with an IC50 value comparable to that of the parent carboxylic acid. These results indicate that the cyclopentane-1,2-dione may be a potentially useful carboxylic acid bio-isostere.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP53949534-B	2-[4-(1-Hydroxy-2-methylpropyl)phenyl]propanoic acid		53949-53-4	Price

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