New 1H-benzo[f]indazole-4,9-diones conjugated with C-protected amino acids and other derivatives: Synthesis and in vitro antiproliferative evaluation

Aurora Molinari, Alfonso Oliva, Marlene Arismendi-Macuer, Leda Guzmán, MAURICIO DANIEL FUENTEALBA CARRASCO, Marcela Knox, Raúl Vinet, Arturo San Feliciano

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

1H-Benzo[f]indazole-4,9-dione derivatives conjugated with C-protected amino acids (glycine, L-alanine, L-phenylalanine and L-glutamic acid) 6a-l were prepared by chemically modifying the prenyl substituent of 3-methyl-7-(4-methylpent-3-enyl)-1H-benzo[f]indazole-4,9- dione 2 through epoxidation, degradative oxidation, oxidation and N-acyl condensation reactions. The chemical structures of the synthesized compounds were elucidated by analyzing their IR, 1H-NMR and 13C-NMR spectral data together with elemental analysis for carbon, hydrogen and nitrogen. The preliminary in vitro antiproliferative activity of the synthesized derivatives was evaluated on KATO-III and MCF-7 cell lines using a cell proliferation assay. The majority of the derivatives exhibited significant antiproliferative activity with IC50 values ranging from 25.5 to 432.5 μM. These results suggest that 1H-benzo[f]indazole-4,9-dione derivatives are promising molecules to be researched for developing new anticancer agents.

Original languageEnglish
Pages (from-to)21924-21938
Number of pages15
JournalMolecules
Volume20
Issue number12
DOIs
StatePublished - 8 Dec 2015

Keywords

  • 1,4-naphthoquinone
  • 1H-benzoindazole
  • Amino acid
  • Pyrazole

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