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Synthesis of Some Nucleoside Analogs via Mannich Reaction of Benzimidazole and Imidazoline Derivatives and Their Characterization as Potential Antimicrobial Agents

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Abstract

The condensation of ethylenediamine or o-phenylenediamine with benzaldehyde or p-bromobenz­aldehyde, respectively, gave the corresponding imidazoline or benzimidazole derivative which was subjected to Mannich aminomethylation to produce new nucleobase analogs. α-D-Glucose was converted to peracetyl derivative, followed by treatment with HBr in acetic acid to obtain 1-bromo sugar. Condensation of the latter with nucleobases afforded new protected nucleoside analogs which were hydrolyzed with sodium methoxide in methanol to obtain free nucleoside analogs. The synthesized compounds were identified by FT-IR and 1H and 13C NMR spectroscopy, and their in vitro antimicrobial activity against four types of bacteria and fungi was evaluated.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, University of Baghdad, Baghdad, Iraq

    H. J. Al-Adhami

  2. Ministry of Education, Directorate of Education of Al-Rusafa the Second, Baghdad, Iraq

    D. J. Mehdi

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  1. H. J. Al-Adhami
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  2. D. J. Mehdi
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Correspondence to H. J. Al-Adhami.

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Al-Adhami, H.J., Mehdi, D.J. Synthesis of Some Nucleoside Analogs via Mannich Reaction of Benzimidazole and Imidazoline Derivatives and Their Characterization as Potential Antimicrobial Agents. Russ J Org Chem 59, 1021–1026 (2023). https://doi.org/10.1134/S1070428023060088

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  • DOI: https://doi.org/10.1134/S1070428023060088

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