2‑Aminooxazole as a Novel Privileged Scaffold
in Antitubercular Medicinal Chemistry
Posted on 2020-06-11 - 19:42
To obtain effective
eradication of numerous infectious diseases
such as tuberculosis, it is important to supply the medicinal chemistry
arsenal with novel chemical agents. Isosterism and bioisosterism are
widely known concepts in the field of early drug discovery, and in
several cases, rational isosteric replacements have contributed to
improved efficacy and physicochemical characteristics throughout the
hit-to-lead optimization process. However, sometimes the synthesis
of isosteres might not be as straightforward as that of the parent
compounds, and therefore, novel synthetic strategies must be elaborated.
In this regard, we herein report the evaluation of a series of N-substituted
4-phenyl-2-aminooxazoles that, despite being isosteres of a widely
used nucleus such as the 2-aminothiazole, have been only seldom explored.
After elaboration of a convenient synthetic strategy, a small set
of 2-aminothiazoles and their 2-aminooxazole counterparts were compared
with regard to antitubercular activity and physicochemical characteristics.
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Azzali, Elisa; Girardini, Miriam; Annunziato, Giannamaria; Pavone, Marialaura; Vacondio, Federica; Mori, Giorgia; et al. (2020). 2‑Aminooxazole as a Novel Privileged Scaffold
in Antitubercular Medicinal Chemistry. ACS Publications. Collection. https://doi.org/10.1021/acsmedchemlett.0c00173