Utility of amino acid coupled 1,2,4-triazoles in organic synthesis: synthesis of some new antileishmainal agents

Abstract

Starting from 3-amino-5-(2-hydroxyphenyl) amino acid coupled triazoles 1a-e, new 3-(2-hydroxyphenyl)-3H-imidazo[2,1-c][1,2,4]triazol-6(5H)-one 2a,b, 3b,d, 6a and 3-N-arly(alkyl) amino acid coupled triazoles 4b,d, 7a,c,d,e have been synthesized as potential antileishmanial agents. The structures of the newly synthesized compounds were confirmed using elemental and spectral analyses (FT-IR, ¹H-NMR, ¹³C-NMR and MS). The in vitro antileishmanial potency of the synthesized compounds was evaluated compared to Amphotericin B deoxycholate and miltefosine as lead references. Compounds 2b, 7d and 7e showed perfect IC₅₀ values corresponding to amphotericin B and more patent than miltefosine against L. aethiopica promastigotes.

KEY WORDS: Amino acids, Coupled, Imidazo-1,2,4-Triazole, Promatigote, Antileishmanial

Bull. Chem. Soc. Ethiop. 2018, 32(3), 559-570.

DOI: https://dx.doi.org/10.4314/bcse.v32i3.14