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Abstract <p>A new approach was proposed for the synthesis of 5-chloro-, 5-bromo-, and 5-iodo-6-aminouracils in high yields by halogenation of 6-aminouracil with the corresponding <i>N</i>-halosuccinimides. For the first time, the constants and thermodynamic characteristics of the acid-base equilibrium of 6-aminouracil and its 5-halogen-substituted derivatives were determined by potentiometric titration in aqueous solutions. The effect of the nature of halogen atoms on the acid-base properties of 6-aminouracil was shown. For the first time, the solubility values in aqueous buffer systems with pH 2.0 and 7.4 at 25 and 37°C, as well as the lipophilicity values of 5-halogen-substituted 6-aminouracils, were determined by high-performance liquid chromatography.</p>

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Synthesis, Acid-Base Properties, Solubility, and Lipophilicity of 6-Amino-5-halogenouracils (Cl, Br, I) in Solutions

  • 期刊论文

  • 发表日期：

    2026年4月23日

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  • Aidar A. Akhiyarov,
  • Inna B. Chernikova,
  • Svetlana F. Petrova,
  • Sergey P. Ivanov

摘要

Abstract

A new approach was proposed for the synthesis of 5-chloro-, 5-bromo-, and 5-iodo-6-aminouracils in high yields by halogenation of 6-aminouracil with the corresponding N-halosuccinimides. For the first time, the constants and thermodynamic characteristics of the acid-base equilibrium of 6-aminouracil and its 5-halogen-substituted derivatives were determined by potentiometric titration in aqueous solutions. The effect of the nature of halogen atoms on the acid-base properties of 6-aminouracil was shown. For the first time, the solubility values in aqueous buffer systems with pH 2.0 and 7.4 at 25 and 37°C, as well as the lipophilicity values of 5-halogen-substituted 6-aminouracils, were determined by high-performance liquid chromatography.