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

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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.

Idioma original	Anglès
Pàgines (de-a)	3661-3674
Revista	Bioorganic and Medicinal Chemistry
Volum	16
Número	7
DOIs	https://doi.org/10.1016/j.bmc.2008.02.011
Estat de la publicació	Publicada - 1 d’abr. 2008

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10.1016/j.bmc.2008.02.011

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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

@article{63df24fa771a484bb30ff13a598b27c8,

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",

year = "2008",

month = apr,

day = "1",

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

language = "English",

volume = "16",

pages = "3661--3674",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

number = "7",

}

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, núm. 7, pàg. 3661-3674. https://doi.org/10.1016/j.bmc.2008.02.011

TY - JOUR

T1 - Synthesis, antimalarial activity, structure-activity relationship analysis of thieno-[3,2-b]benzothiazine S,S-dioxide analogs

AU - Barazarte, Arthur

AU - Camacho, José

AU - Domínguez, José

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

PY - 2008/4/1

Y1 - 2008/4/1

N2 - 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.

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

KW - Thieno

UR - https://www.scopus.com/pages/publications/41649110228

U2 - 10.1016/j.bmc.2008.02.011

DO - 10.1016/j.bmc.2008.02.011

M3 - Article

SN - 0968-0896

VL - 16

SP - 3661

EP - 3674

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 7

ER -

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

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