Synthesis, antimalarial activity, structure-activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs

Arthur Barazarte, José Camacho, José Domínguez, Gricela Lobo, Neira Gamboa, Juan Rodrigues, Mario V. Capparelli, Ángel Álvarez-Larena, Sebastian Andujar, Daniel Enriz, Jaime Charris

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    Abstract

    An improved procedure for the synthesis of 3-amino-9-arylsubstituted-thieno[3,2-b]benzothiazine S,S-dioxide 2-decarboxylated is reported. Thieno-[3,2-b]benzothiazine S,S-dioxide derivatives were investigated for their abilities to inhibit β-hematin formation, hemoglobin hydrolysis and in vivo for their efficacy in rodent Plasmodium berghei. Compounds 5j-o were the most promising as inhibitors of hemoglobin hydrolysis, however, the compounds are not as efficient as chloroquine. A structure-activity relationship (SAR) study was carried out in this series. Our results allow us to determine the minimal structural requirements to produce the biological response. © 2008 Elsevier Ltd. All rights reserved.
    Original languageEnglish
    Pages (from-to)3661-3674
    JournalBioorganic and Medicinal Chemistry
    Volume16
    Issue number7
    DOIs
    Publication statusPublished - 1 Apr 2008

    Keywords

    • 1,4-Benzothiazines
    • Antimalarial
    • Cyclization
    • SAR study
    • Thieno

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    Barazarte, A., Camacho, J., Domínguez, J., Lobo, G., Gamboa, N., Rodrigues, J., Capparelli, M. V., Álvarez-Larena, Á., Andujar, S., Enriz, D., & Charris, J. (2008). Synthesis, antimalarial activity, structure-activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs. Bioorganic and Medicinal Chemistry, 16(7), 3661-3674. https://doi.org/10.1016/j.bmc.2008.02.011