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Syntheses and electrochemical properties of novel aminopyrimidinone derivatives as a new class of abasic-site binders

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Abstract

We describe syntheses and electrochemical properties of a new class of aminopyrimidinone derivatives: 2-amino-4-(3′,4′-dimethoxyphenyl)-6-pyrimidinone, 2-amino-4-(3′,4′-dihydroxyphenyl)-6-pyrimidinone, 2,4-diamino-5-(3′,4′-dimethoxyphenyl)-6-pyrimidinone, 2,4-diamino-5-(3′,4′-dihydroxyphenyl)-6-pyrimidinone, and 4-amino-5-(3′,4′-dihydroxyphenyl)-2,6-pyrimidinione, three of which possess a catechol unit as an oxidation-active moiety for developing electrochemically detectable abasic-site binders. These compounds were synthesized via a pyrimidine-ring forming reaction with guanidine. Cyclic voltammetry measurements revealed that the catechol-bearing derivatives showed oxidation potentials lower than that of DNA, indicating that they satisfied the requirements for the purpose.

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Authors and Affiliations

  1. Graduate School of Pharmaceutical Sciences, University of Toyama, Sugitani 2630, Toyama, 930-0194, Japan

    Junya Chiba, Yasuhiro Doi & Masahiko Inouye

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  1. Junya Chiba
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  2. Yasuhiro Doi
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  3. Masahiko Inouye
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Correspondence to Junya Chiba or Masahiko Inouye.

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Chiba, J., Doi, Y. & Inouye, M. Syntheses and electrochemical properties of novel aminopyrimidinone derivatives as a new class of abasic-site binders. Res Chem Intermed 39, 177–183 (2013). https://doi.org/10.1007/s11164-012-0641-7

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  • DOI: https://doi.org/10.1007/s11164-012-0641-7

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