The frequent use of carboxylic acids in biologically-active molecules has led to the identification of numerous acid bioisosteres. One potential acid bioisostere, the tetrazolone (tetrazol-5-one) group, is related to the more common tetrazole motif. In this paper, we describe the late-stage functionalization of marketed drugs to make tetrazolone congeners of pharmaceuticals containing a carboxylic acid. We continue, by describing some attractions of using a tetrazolone as an acid bioisostere, and discuss the biological profile with tetrazolone analogs of marketed drugs such as Telmisartan (AT1 antagonist), monomethylfumarate (activator of Nrf2), and Bexarotene (RXR agonist), amongst others.

Late-stage functionalization of marketed drugs: Synthesis and use of tetrazolones as a carboxylic acid bioisostere

252nd National Meeting (2016)

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