Synthesis via “click chemistry" of new triazole analogues derivatives of grandisin and veraguensin neolignans with potential trypanocidal and leishmanicidal activity

Abstract

Using the concept of bioisosterism, new triazole analogs were designed from the molecular modification of grandisin and veraguensin neolignans which have a furan group that is a bioisóstere of 1,2,3-triazoles ring. In order to obtain more potent compounds, with fewer side effects, and better physical and chemical characteristics in combating leishmaniasis and chagas disease, this research group synthesized, via "Click Chemistry", eight new triazole analogues of neolignans. Thus reactions 1,3-dipolar cycloaddition of Huisgen were performed between terminal acetylenes and azides previously synthesized. The catalytic system CuSO4.5H2O/Ascorbate Sodium / CH2Cl2/H2O was used and, under this reaction conditions eight triazole analogues were synthesized in good yields. Trypanocidal activity test showed positive for the eight molecules.

Keywords

• bioisosterism
• triazole analogs
• click chemistry