Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide

A simple synthesis and study by UV-vis, IR, NMR, ESI-CID-MS2 and X-ray diffraction of ((2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl}ethylidene)hydrazinecarbothioamide is reported. It was tested in vitro against chloroquine-resistant strain (W2) of Plasmodium falciparum, hemozoin (β-hem...

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Autores: Parra, Yonathan de J., Ferrer, Rosa Elena, Bruno-Colmenarez, Julia, Charris, Jaime, Lobo, Gricela, de Domínguez, Neira Gamboa, Rosenthal, Philip J., Gut, Jiri
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2017
País:Brasil
Institución:Universidade Federal de Mato Grosso do Sul (UFMS)
Repositorio:Orbital - The Electronic Journal of Chemistry (Campo Grande)
Idioma:inglés
OAI Identifier:oai:periodicos.ufms.br:article/16457
Acceso en línea:https://periodicos.ufms.br/index.php/orbital/article/view/16457
Access Level:acceso abierto
Palabra clave:thiosemicarbazones
antimalarial activity
crystal structure
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spelling Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamidethiosemicarbazonesantimalarial activitycrystal structureA simple synthesis and study by UV-vis, IR, NMR, ESI-CID-MS2 and X-ray diffraction of ((2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl}ethylidene)hydrazinecarbothioamide is reported. It was tested in vitro against chloroquine-resistant strain (W2) of Plasmodium falciparum, hemozoin (β-hematin) formation and cysteine protease falcipain-2. In general, it was found to possess a proved activity in its inhibitory power on the parasite but less active on the formation of hemozoin (β-hematin) and falcipain-2. Also, the X-ray analysis presented an unexpected electronic density that can be assigned like S(2). This electronic density can be attributed to autocondensation of thiosemicarbazide, generating H2S as a subproduct. DOI: http://dx.doi.org/10.17807/orbital.v9i4.1001Instituto de Química, Universidade Federal de Mato Grosso do Sul2017-10-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionPeer-reviewedapplication/pdfapplication/pdfhttps://periodicos.ufms.br/index.php/orbital/article/view/16457Orbital: The Electronic Journal of Chemistry; Orbital - Vol. 9 No. 4 - July - September 2017; 308-314Orbital: The Electronic Journal of Chemistry; Orbital - Vol. 9 No. 4 - July - September 2017; 308-3141984-6428reponame:Orbital - The Electronic Journal of Chemistry (Campo Grande)instname:Universidade Federal de Mato Grosso do Sul (UFMS)instacron:UFMSenghttps://periodicos.ufms.br/index.php/orbital/article/view/16457/11148https://periodicos.ufms.br/index.php/orbital/article/view/16457/11149Copyright (c) 2017 Orbital: The Electronic Journal of Chemistryhttps://creativecommons.org/licenses/by-nc-nd/4.0info:eu-repo/semantics/openAccessParra, Yonathan de J.Ferrer, Rosa ElenaBruno-Colmenarez, JuliaCharris, JaimeLobo, Gricelade Domínguez, Neira GamboaRosenthal, Philip J.Gut, Jiri2023-01-20T10:57:42Zoai:periodicos.ufms.br:article/16457Revistahttps://periodicos.ufms.br/index.php/orbital/indexPUBhttps://periodicos.ufms.br/index.php/orbital/oaieditor.orbital@ufms.br || marcos.amaral@ufms.br1984-64281984-6428opendoar:2023-01-20T10:57:42Orbital - The Electronic Journal of Chemistry (Campo Grande) - Universidade Federal de Mato Grosso do Sul (UFMS)false
dc.title.none.fl_str_mv Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide
title Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide
spellingShingle Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide
Parra, Yonathan de J.
thiosemicarbazones
antimalarial activity
crystal structure
title_short Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide
title_full Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide
title_fullStr Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide
title_full_unstemmed Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide
title_sort Synthesis, Characterization, Crystal Structure and Antimalarial Activity of (2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl} ethylidene)hydrazine Carbothioamide
dc.creator.none.fl_str_mv Parra, Yonathan de J.
Ferrer, Rosa Elena
Bruno-Colmenarez, Julia
Charris, Jaime
Lobo, Gricela
de Domínguez, Neira Gamboa
Rosenthal, Philip J.
Gut, Jiri
author Parra, Yonathan de J.
author_facet Parra, Yonathan de J.
Ferrer, Rosa Elena
Bruno-Colmenarez, Julia
Charris, Jaime
Lobo, Gricela
de Domínguez, Neira Gamboa
Rosenthal, Philip J.
Gut, Jiri
author_role author
author2 Ferrer, Rosa Elena
Bruno-Colmenarez, Julia
Charris, Jaime
Lobo, Gricela
de Domínguez, Neira Gamboa
Rosenthal, Philip J.
Gut, Jiri
author2_role author
author
author
author
author
author
author
dc.subject.por.fl_str_mv thiosemicarbazones
antimalarial activity
crystal structure
topic thiosemicarbazones
antimalarial activity
crystal structure
description A simple synthesis and study by UV-vis, IR, NMR, ESI-CID-MS2 and X-ray diffraction of ((2E)-2-(1-{4-[(7-chloroquinolin-4-yl)amino]phenyl}ethylidene)hydrazinecarbothioamide is reported. It was tested in vitro against chloroquine-resistant strain (W2) of Plasmodium falciparum, hemozoin (β-hematin) formation and cysteine protease falcipain-2. In general, it was found to possess a proved activity in its inhibitory power on the parasite but less active on the formation of hemozoin (β-hematin) and falcipain-2. Also, the X-ray analysis presented an unexpected electronic density that can be assigned like S(2). This electronic density can be attributed to autocondensation of thiosemicarbazide, generating H2S as a subproduct. DOI: http://dx.doi.org/10.17807/orbital.v9i4.1001
publishDate 2017
dc.date.none.fl_str_mv 2017-10-02
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Peer-reviewed
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv https://periodicos.ufms.br/index.php/orbital/article/view/16457
url https://periodicos.ufms.br/index.php/orbital/article/view/16457
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv https://periodicos.ufms.br/index.php/orbital/article/view/16457/11148
https://periodicos.ufms.br/index.php/orbital/article/view/16457/11149
dc.rights.driver.fl_str_mv Copyright (c) 2017 Orbital: The Electronic Journal of Chemistry
https://creativecommons.org/licenses/by-nc-nd/4.0
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Copyright (c) 2017 Orbital: The Electronic Journal of Chemistry
https://creativecommons.org/licenses/by-nc-nd/4.0
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Instituto de Química, Universidade Federal de Mato Grosso do Sul
publisher.none.fl_str_mv Instituto de Química, Universidade Federal de Mato Grosso do Sul
dc.source.none.fl_str_mv Orbital: The Electronic Journal of Chemistry; Orbital - Vol. 9 No. 4 - July - September 2017; 308-314
Orbital: The Electronic Journal of Chemistry; Orbital - Vol. 9 No. 4 - July - September 2017; 308-314
1984-6428
reponame:Orbital - The Electronic Journal of Chemistry (Campo Grande)
instname:Universidade Federal de Mato Grosso do Sul (UFMS)
instacron:UFMS
instname_str Universidade Federal de Mato Grosso do Sul (UFMS)
instacron_str UFMS
institution UFMS
reponame_str Orbital - The Electronic Journal of Chemistry (Campo Grande)
collection Orbital - The Electronic Journal of Chemistry (Campo Grande)
repository.name.fl_str_mv Orbital - The Electronic Journal of Chemistry (Campo Grande) - Universidade Federal de Mato Grosso do Sul (UFMS)
repository.mail.fl_str_mv editor.orbital@ufms.br || marcos.amaral@ufms.br
_version_ 1853664387305308160
score 15,301603

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