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

doi:10.1016/j.bmc.2008.02.011

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

Research output: Contribution to journal › Article › Research › peer-review

31 Citations (Scopus)

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 language	English
Pages (from-to)	3661-3674
Journal	Bioorganic and Medicinal Chemistry
Volume	16
Issue number	7
DOIs	https://doi.org/10.1016/j.bmc.2008.02.011
Publication status	Published - 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

Barazarte, Arthur ; Camacho, José ; Domínguez, José ; Lobo, Gricela ; Gamboa, Neira ; Rodrigues, Juan ; Capparelli, Mario V. ; Álvarez-Larena, Ángel ; Andujar, Sebastian ; Enriz, Daniel ; Charris, Jaime. / Synthesis, antimalarial activity, structure-activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs. In: Bioorganic and Medicinal Chemistry. 2008 ; Vol. 16, No. 7. pp. 3661-3674.

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

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. {\textcopyright} 2008 Elsevier Ltd. All rights reserved.",

keywords = "1,4-Benzothiazines, Antimalarial, Cyclization, SAR study, Thieno",

author = "Arthur Barazarte and Jos{\'e} Camacho and Jos{\'e} Dom{\'i}nguez and Gricela Lobo and Neira Gamboa and Juan Rodrigues and Capparelli, {Mario V.} and {\'A}ngel {\'A}lvarez-Larena and Sebastian Andujar and Daniel Enriz and Jaime Charris",

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doi = "10.1016/j.bmc.2008.02.011",

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Barazarte, A, Camacho, J, Domínguez, J, Lobo, G, Gamboa, N, Rodrigues, J, Capparelli, MV, 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, vol. 16, no. 7, pp. 3661-3674. https://doi.org/10.1016/j.bmc.2008.02.011

Synthesis, antimalarial activity, structure-activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs. / Barazarte, Arthur; Camacho, José; Domínguez, José; Lobo, Gricela; Gamboa, Neira; Rodrigues, Juan; Capparelli, Mario V.; Álvarez-Larena, Ángel; Andujar, Sebastian; Enriz, Daniel; Charris, Jaime.

In: Bioorganic and Medicinal Chemistry, Vol. 16, No. 7, 01.04.2008, p. 3661-3674.

Research output: Contribution to journal › Article › Research › peer-review

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AU - Barazarte, Arthur

AU - Camacho, José

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AU - Lobo, Gricela

AU - Gamboa, Neira

AU - Rodrigues, Juan

AU - Capparelli, Mario V.

AU - Álvarez-Larena, Ángel

AU - Andujar, Sebastian

AU - Enriz, Daniel

AU - Charris, Jaime

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AB - 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.

KW - 1,4-Benzothiazines

KW - Antimalarial

KW - Cyclization

KW - SAR study

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