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

Abstract

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.

Mechanochemical Synthesis and Biological Evaluation of Novel Isoniazid Derivatives with Potent Antitubercular Activity

“…Our group is involved both in synthesizing new antitubercular compounds, including cinnamic acid derivatives [ 26 , 27 , 28 , 29 ], triazoles [ 30 , 31 , 32 , 33 ], pyrrolidines [ 34 , 35 , 36 ], semicarbazones and hydrazine/hydrazones [ 37 ], and in searching for new and innovative synthetic reactions. We have recently reported the solvent-free mechanosynthesis of a series of hydrazones [ 38 , 39 ].…”