Medicinal Chemistry Research

, Volume 24, Issue 1, pp 430–441

Long-chain alkyltriazoles as antitumor agents: synthesis, physicochemical properties, and biological and computational evaluation

  • Vanessa Silva Gontijo
  • Michael Éder Oliveira
  • Rafael José Resende
  • Amanda Luisa Fonseca
  • Renata Rachide Nunes
  • Moacyr Comar Júnior
  • Alex Gutterres Taranto
  • Natalia Machado Pereira Oliveira Torres
  • Gustavo Henrique Ribeiro Viana
  • Luciana Maria Silva
  • Rosemeire Brondi Alves
  • Fernando Pilla Varotti
  • Rossimiriam Pereira Freitas
Original Research

DOI: 10.1007/s00044-014-1137-3

Cite this article as:
Gontijo, V.S., Oliveira, M.É., Resende, R.J. et al. Med Chem Res (2015) 24: 430. doi:10.1007/s00044-014-1137-3

Abstract

A series of novel long-chain alkyltriazoles were prepared from commercial diols in a rapid process with good yields. The compounds were evaluated in vitro for their anticancer potential against two human cancer cell lines: colon carcinoma (RKO) and uterine carcinoma (HeLa). The results of colorimetric MTT assays showed that six of fourteen compounds tested decreased cell viability in these cell lines. Compounds 5e and 6a were the most active against RKO cells, with IC50 values of 16.70 and 14.57 μM, respectively. The same compounds, 5e and 6a, were the most active in HeLa cells as well, with IC50 values of 11.05 and 12.77 μM, respectively. In addition, compound 5e was found to induce apoptosis in RKO cells, as assessed by TUNEL assay. The results suggest that compound 5e may be a promising prototype anticancer agent.

Keywords

AlkyltriazolesAntitumoralClick chemistryHeterocycles

Supplementary material

44_2014_1137_MOESM1_ESM.docx (22.6 mb)
Supplementary material 1 (DOCX 23143 kb)

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Vanessa Silva Gontijo
    • 1
  • Michael Éder Oliveira
    • 2
  • Rafael José Resende
    • 2
  • Amanda Luisa Fonseca
    • 2
  • Renata Rachide Nunes
    • 2
  • Moacyr Comar Júnior
    • 2
  • Alex Gutterres Taranto
    • 2
  • Natalia Machado Pereira Oliveira Torres
    • 1
  • Gustavo Henrique Ribeiro Viana
    • 2
  • Luciana Maria Silva
    • 3
  • Rosemeire Brondi Alves
    • 1
  • Fernando Pilla Varotti
    • 2
  • Rossimiriam Pereira Freitas
    • 1
  1. 1.Departamento de Química, ICExUFMGBelo HorizonteBrazil
  2. 2.Universidade Federal de São João del-ReiDivinópolisBrazil
  3. 3.Laboratório de Biologia CelularFundação Ezequiel DiasBelo HorizonteBrazil