Tetrazoles as carboxylic acid isosteres: chemistry and biology

Tetrazoles are often used as metabolism-resistant isosteric replacements for carboxylic acids in SAR-driven medicinal chemistry analogue syntheses. Tetrazoles have not been found in nature; with rare exceptions, these compounds do not exhibit appreciable biological activity, but they are at the same...

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Bibliographic Details
Published inJournal of inclusion phenomena and macrocyclic chemistry Vol. 78; no. 1-4; pp. 15 - 37
Main Authors Malik, Maqsood Ahmad, Wani, Mohmmad Younus, Al-Thabaiti, Shaeel Ahmed, Shiekh, Rayees Ahmad
Format Journal Article
LanguageEnglish
Published Dordrecht Springer Netherlands 01.04.2014
Subjects
Chemistry
Chemistry and Materials Science
Crystallography and Scattering Methods
Food Science
Organic Chemistry
Review Article
Biological properties
Bioisosterism
Synthesis
Tetrazole
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Summary:Tetrazoles are often used as metabolism-resistant isosteric replacements for carboxylic acids in SAR-driven medicinal chemistry analogue syntheses. Tetrazoles have not been found in nature; with rare exceptions, these compounds do not exhibit appreciable biological activity, but they are at the same time resistant to biological degradation. This property makes it possible to use tetrazoles as isosteric substituents of various functional groups in the development of biologically active substances. The tetrazole motif has been used in various drug pharmacophores as a suitable replacement of carboxylic acid moiety and different methods have been used for the synthesis of tetrazoles using different reaction conditions. This review tries to give a vivid look on the different synthetic methods, using catalysts or different reagents for the synthesis of tetrazoles. The biological importance of tetrazoles has also been highlighted.
ISSN:1388-3127
1573-1111
DOI:10.1007/s10847-013-0334-x