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Synthesis and biological activity of 1,3,5-triazino[1,2-a]benzimidazol-2-amines

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Abstract

Several 4-substituted 1,3,5-triazino[1,2-a]benzimidazol-2-amines were prepared via cyclization of 2-benzimidazolylguanidine with various reactants. The prototropic tautomerism in the obtained dihydro analogs was investigated. According to the NMR data, the 3,4-dihydro form was found to predominate in DMSO solutions. All tested compounds inhibited the activity of mammalian dihydrofolate reductase. The most active compound was 4,4-dimethyl-3,4-dihydro[1,3,5]triazino[1,2-a]benzimidazol-2-amine (IC50 = 10.9 mM).

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, Perm, Russian Federation

    A. V. Dolzhenko

  2. Department of Pharmacy, National University of Singapore, Singapore

    A. V. Dolzhenko & W. K. Chui

Authors
  1. A. V. Dolzhenko
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  2. W. K. Chui
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Correspondence to A. V. Dolzhenko.

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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 41, No. 9, pp. 17–19, September, 2007.

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Dolzhenko, A.V., Chui, W.K. Synthesis and biological activity of 1,3,5-triazino[1,2-a]benzimidazol-2-amines. Pharm Chem J 41, 470–473 (2007). https://doi.org/10.1007/s11094-007-0103-5

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  • DOI: https://doi.org/10.1007/s11094-007-0103-5

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