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      Tetrazoles via Multicomponent Reactions

      review-article
      , ,
      Chemical Reviews
      American Chemical Society

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          Abstract

          Tetrazole derivatives are a prime class of heterocycles, very important to medicinal chemistry and drug design due to not only their bioisosterism to carboxylic acid and amide moieties but also to their metabolic stability and other beneficial physicochemical properties. Although more than 20 FDA-approved drugs contain 1 H- or 2 H-tetrazole substituents, their exact binding mode, structural biology, 3D conformations, and in general their chemical behavior is not fully understood. Importantly, multicomponent reaction (MCR) chemistry offers convergent access to multiple tetrazole scaffolds providing the three important elements of novelty, diversity, and complexity, yet MCR pathways to tetrazoles are far from completely explored. Here, we review the use of multicomponent reactions for the preparation of substituted tetrazole derivatives. We highlight specific applications and general trends holding therein and discuss synthetic approaches and their value by analyzing scope and limitations, and also enlighten their receptor binding mode. Finally, we estimated the prospects of further research in this field.

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                Author and article information

                Journal
                Chem Rev
                Chem. Rev
                cr
                chreay
                Chemical Reviews
                American Chemical Society
                0009-2665
                1520-6890
                01 February 2019
                13 February 2019
                : 119
                : 3
                : 1970-2042
                Affiliations
                [1]Drug Design Group, Department of Pharmacy, University of Groningen , Antonius Deusinglaan 1, 9700 AD Groningen, The Netherlands
                Author notes
                [* ]Phone: (+31)50-3633307. E-mail: a.s.s.domling@ 123456rug.nl .
                Article
                10.1021/acs.chemrev.8b00564
                6376451
                30707567
                85c6df2f-109f-4daf-aa35-e840eb136ddc
                Copyright © 2019 American Chemical Society

                This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License, which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.

                History
                : 13 September 2018
                Categories
                Review
                Custom metadata
                cr8b00564
                cr-2018-00564d

                Chemistry
                Chemistry

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