Synthesis and Characterization of Some Novel 2-(Trifluoromethyl)pyrimido[1,2-a]benzimidazoles and Pyrimido[1,2-a]benzimidazol-2H)-ones of Biological Interest

Nilo Zanatta; Simone S. Amaral; Andressa Esteves-Souza; Aurea Echevarria; Patrícia B. Brondani; Darlene C. Flores; Helio G. Bonacorso; Alex F. C. Flores; Marcos A. P. Martins

doi:10.1055/s-2006-942444

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Synthesis 2006(14): 2305-2312
DOI: 10.1055/s-2006-942444

PAPER

Synthesis and Characterization of Some Novel 2-(Trifluoromethyl)pyrimido[1,2-a]benzimidazoles and Pyrimido[1,2-a]benzimidazol-2H)-ones of Biological Interest

Nilo Zanatta*^a, Simone S. Amaral^a, Andressa Esteves-Souza^b, Aurea Echevarria*^b, Patrícia B. Brondani^a, Darlene C. Flores^a, Helio G. Bonacorso^a, Alex F. C. Flores^a, Marcos A. P. Martins^a
^a Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97.105-900, Santa Maria, RS, Brazil
Fax: +55(55)2208031; e-Mail: zanatta@base.ufsm.br;
^b Departamento de Química, Universidade Federal Rural do Rio de Janeiro, 23851-970, Seropédica, RJ, Brazil
e-Mail: echevarr@ufrrj.br;

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Publication History

Received 24 February 2006
Publication Date:
28 June 2006 (online)

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Abstract

The synthesis of some potentially active 2-(trifluoromethyl)pyrimido[1,2-a]benzimidazoles and pyrimido[1,2-a]benzimidazol-2(1H)-ones by the cyclization of 4-alkoxyvinyl trifluoro(chloro)methyl ketones with 2-aminobenzimidazole is described. The structure of the products was assigned based on ¹H and ¹³C NMR as well as 2D-NMR experiments. Some of the obtained products exhibited significant DNA-topoisomerase I inhibitory activity.

Key words

2-aminobenzimidazole - pyrimidobenzimidazole - enones - halogenated heterocycles - DNA-topoisomerase I inhibitory activity

References

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