Synthesis and evaluation of β-hydroxytriazoles and related compounds as antitubercular agents

Menendez, C., Mori, G., Maillot, M., Fabing, I., Carayon, C., Silvia Orena, B., Rosalia Pasca, M., Voitenko, Z., Lherbet, C., Baltas, M. (2015). Synthesis and evaluation of β-hydroxytriazoles and related compounds as antitubercular agents. French-Ukrainian Journal of Chemistry, 3(1), 82–96. https://doi.org/10.17721/fujcV3I1P82-96

A new series of β-hydroxytriazoles were synthesized and evaluated as Mycobacterium tuberculosis inhibitors. Our strategy implied the synthesis of alkyne precursors through a Barbier reaction between benzaldehydes and propargyl bromide followed by click chemistry to afford substituted β-hydroxyl benzyltriazoles. These compounds are also key intermediates either for oxidation reactions leading to α,β-diketotriazoles or for elimination reactions affording styryl triazoles. Evaluation of all new compounds for in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv resulted in compounds with MIC up to 7 μM.