title: 1,2,3-triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones.
abstract: 1,2,3-Triazole-, arylamino- and thio-substituted naphthoquinones (24, 8, and 2 representatives, respectively) were synthesized in moderate yields and evaluated against several human cancer cell lines (blood, ovarian, breast, central nervous system, colon, and prostate cancers and melanoma), showing, for some of them, IC50 values below 2 μM. The cytotoxic potential of the tested naphthoquinones was also assayed on non-tumor cells such as human peripheral blood mononucluear cells (PBMC) and two murine fibroblast lines (L929 and V79 cells). α-Lapachone- and nor-α-lapachone-based 1,2,3-triazoles and arylamino-substituted naphthoquinones showed potent cytotoxicity against different cancer cell lines. The compounds may represent promising new lead derivatives for anticancer drug development. The electrochemical properties of selected compounds were evaluated in an attempt to correlate them with antitumor activity.
authors: Instituto de Ciências Exatas, Departamento de Química, UFMG, 31270-901 Belo Horizonte, MG, Brazil.
authors: Eduardo H G
authors: EH
authors: da Cruz
authors: Instituto de Ciências Exatas, Departamento de Química, UFMG, 31270-901 Belo Horizonte, MG, Brazil.
authors: Caio M B
authors: CM
authors: Hussene
authors: Instituto de Ciências Exatas, Departamento de Química, UFMG, 31270-901 Belo Horizonte, MG, Brazil.
authors: Gleiston G
authors: GG
authors: Dias
authors: Instituto de Ciências Exatas, Departamento de Química, UFMG, 31270-901 Belo Horizonte, MG, Brazil.
authors: Emilay B T
authors: EB
authors: Diogo
authors: Instituto de Ciências Exatas, Departamento de Química, UFMG, 31270-901 Belo Horizonte, MG, Brazil.
authors: Isadora M M
authors: IM
authors: de Melo
authors: Instituto de Ciências Exatas, Departamento de Química, UFMG, 31270-901 Belo Horizonte, MG, Brazil.
authors: Bernardo L
authors: BL
authors: Rodrigues
authors: Departamento de Química Fundamental, UFPE, 50670-901 Recife, PE, Brazil.
authors: Mauro G
authors: MG
authors: da Silva
authors: Departamento de Ciências Moleculares, UFRPE, 52171-900 Recife, PE, Brazil.
authors: Wagner O
authors: WO
authors: Valença
authors: Departamento de Ciências Moleculares, UFRPE, 52171-900 Recife, PE, Brazil.
authors: Celso A
authors: CA
authors: Camara
authors: Departamento de Ciências Moleculares, UFRPE, 52171-900 Recife, PE, Brazil.
authors: Ronaldo N
authors: RN
authors: de Oliveira
authors: Instituto de Química e Biotecnologia, UFAL, Tabuleiro do Martins, 57072-970 Maceió, AL, Brazil.
authors: Yen G
authors: YG
authors: de Paiva
authors: Instituto de Química e Biotecnologia, UFAL, Tabuleiro do Martins, 57072-970 Maceió, AL, Brazil.
authors: Marilia O F
authors: MO
authors: Goulart
authors: Laboratório Nacional de Oncologia Experimental, Departamento de Fisiologia e Farmacologia, UFC, 60430-270 Fortaleza, CE, Brazil.
authors: Bruno C
authors: BC
authors: Cavalcanti
authors: Laboratório Nacional de Oncologia Experimental, Departamento de Fisiologia e Farmacologia, UFC, 60430-270 Fortaleza, CE, Brazil.
authors: Claudia
authors: C
authors: Pessoa
authors: Instituto de Ciências Exatas, Departamento de Química, UFMG, 31270-901 Belo Horizonte, MG, Brazil. Electronic address: eufranio@ufmg.br.
authors: Eufrânio N
authors: EN
authors: da Silva Júnior
mesh_terms: D049109:Cell Proliferation; D057930:Click Chemistry; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D009285:Naphthoquinones / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry*
chemical_list: D009285:Naphthoquinones; D014230:Triazoles
keywords: 1,2,3-Triazoles; 1,4-Naphthoquinone; Cancer; Click chemistry; Lapachol