Mefloquine–Oxazolidine derivatives : a new class of anticancer agents

Detalhes bibliográficos
Autor(a) principal: Rodrigues, Felipe A. R.
Data de Publicação: 2014
Outros Autores: Bomfim, Igor da S., Cavalcanti, Bruno C., Pessoa, Claudia, Goncalves, Raoni S. B., Wardell, James L., Wardel, Solange M. S. V., Souza, Marcus V. N. de
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da Universidade Federal do Ceará (UFC)
Texto Completo: http://www.repositorio.ufc.br/handle/riufc/7215
Resumo: A series of 23 racemic mefloquine–oxazolidine derivatives, 4-[3-(aryl)hexahydro[1,3]oxazolo[3,4-a]pyridin- 1-yl]-2,8-bis(trifluoromethyl)quinolines, derived from (R*, S*)-(±)-mefloquine and arenealdehydes, have been evaluated for their activity against four cancer cell lines (HCT-8, OVCAR-8, HL-60, and SF-295). Good cytotoxicities have been determined with IC50 values ranging from 0.59 to 4.79 lg/mL. In general compounds with aryl groups having strong electron-releasing substituents, such as HO and MeO, or electron-rich heteroaryl groups, for example imidazol-2-y-l, are active. However, other factors such as steric effects may play a role. As both the active and non-active conformations of the mefloquine–oxazolidine derivatives are similar, it is concluded that molecular conformations do not play a significant role either. This study is the first to evaluate mefloquine derivatives as antitumor agents. The mefloquine–oxazolidine derivatives are considered to be useful leads for the rational design of new antitumor agents.
id UFC-7_427955369157b004e6f4898a31dd2b4c
oai_identifier_str oai:repositorio.ufc.br:riufc/7215
network_acronym_str UFC-7
network_name_str Repositório Institucional da Universidade Federal do Ceará (UFC)
repository_id_str
spelling Mefloquine–Oxazolidine derivatives : a new class of anticancer agentsMefloquinaA series of 23 racemic mefloquine–oxazolidine derivatives, 4-[3-(aryl)hexahydro[1,3]oxazolo[3,4-a]pyridin- 1-yl]-2,8-bis(trifluoromethyl)quinolines, derived from (R*, S*)-(±)-mefloquine and arenealdehydes, have been evaluated for their activity against four cancer cell lines (HCT-8, OVCAR-8, HL-60, and SF-295). Good cytotoxicities have been determined with IC50 values ranging from 0.59 to 4.79 lg/mL. In general compounds with aryl groups having strong electron-releasing substituents, such as HO and MeO, or electron-rich heteroaryl groups, for example imidazol-2-y-l, are active. However, other factors such as steric effects may play a role. As both the active and non-active conformations of the mefloquine–oxazolidine derivatives are similar, it is concluded that molecular conformations do not play a significant role either. This study is the first to evaluate mefloquine derivatives as antitumor agents. The mefloquine–oxazolidine derivatives are considered to be useful leads for the rational design of new antitumor agents.1747-02772014-02-07T11:52:16Z2014-02-07T11:52:16Z2014info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfRODRIGUES, F. A. R. et al. Mefloquine–Oxazolidine derivatives : a new class of anticancer agents. Chemical Biology & Drug Design, Oxford, Inglaterra, v. 83, n. 1, p. 126-131, 2014.1747-0277http://www.repositorio.ufc.br/handle/riufc/7215Rodrigues, Felipe A. R.Bomfim, Igor da S.Cavalcanti, Bruno C.Pessoa, ClaudiaGoncalves, Raoni S. B.Wardell, James L.Wardel, Solange M. S. V.Souza, Marcus V. N. deengreponame:Repositório Institucional da Universidade Federal do Ceará (UFC)instname:Universidade Federal do Ceará (UFC)instacron:UFCinfo:eu-repo/semantics/openAccess2019-01-15T16:28:10Zoai:repositorio.ufc.br:riufc/7215Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2024-09-11T18:19:12.269072Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false
dc.title.none.fl_str_mv Mefloquine–Oxazolidine derivatives : a new class of anticancer agents
title Mefloquine–Oxazolidine derivatives : a new class of anticancer agents
spellingShingle Mefloquine–Oxazolidine derivatives : a new class of anticancer agents
Rodrigues, Felipe A. R.
Mefloquina
title_short Mefloquine–Oxazolidine derivatives : a new class of anticancer agents
title_full Mefloquine–Oxazolidine derivatives : a new class of anticancer agents
title_fullStr Mefloquine–Oxazolidine derivatives : a new class of anticancer agents
title_full_unstemmed Mefloquine–Oxazolidine derivatives : a new class of anticancer agents
title_sort Mefloquine–Oxazolidine derivatives : a new class of anticancer agents
author Rodrigues, Felipe A. R.
author_facet Rodrigues, Felipe A. R.
Bomfim, Igor da S.
Cavalcanti, Bruno C.
Pessoa, Claudia
Goncalves, Raoni S. B.
Wardell, James L.
Wardel, Solange M. S. V.
Souza, Marcus V. N. de
author_role author
author2 Bomfim, Igor da S.
Cavalcanti, Bruno C.
Pessoa, Claudia
Goncalves, Raoni S. B.
Wardell, James L.
Wardel, Solange M. S. V.
Souza, Marcus V. N. de
author2_role author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Rodrigues, Felipe A. R.
Bomfim, Igor da S.
Cavalcanti, Bruno C.
Pessoa, Claudia
Goncalves, Raoni S. B.
Wardell, James L.
Wardel, Solange M. S. V.
Souza, Marcus V. N. de
dc.subject.por.fl_str_mv Mefloquina
topic Mefloquina
description A series of 23 racemic mefloquine–oxazolidine derivatives, 4-[3-(aryl)hexahydro[1,3]oxazolo[3,4-a]pyridin- 1-yl]-2,8-bis(trifluoromethyl)quinolines, derived from (R*, S*)-(±)-mefloquine and arenealdehydes, have been evaluated for their activity against four cancer cell lines (HCT-8, OVCAR-8, HL-60, and SF-295). Good cytotoxicities have been determined with IC50 values ranging from 0.59 to 4.79 lg/mL. In general compounds with aryl groups having strong electron-releasing substituents, such as HO and MeO, or electron-rich heteroaryl groups, for example imidazol-2-y-l, are active. However, other factors such as steric effects may play a role. As both the active and non-active conformations of the mefloquine–oxazolidine derivatives are similar, it is concluded that molecular conformations do not play a significant role either. This study is the first to evaluate mefloquine derivatives as antitumor agents. The mefloquine–oxazolidine derivatives are considered to be useful leads for the rational design of new antitumor agents.
publishDate 2014
dc.date.none.fl_str_mv 2014-02-07T11:52:16Z
2014-02-07T11:52:16Z
2014
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv RODRIGUES, F. A. R. et al. Mefloquine–Oxazolidine derivatives : a new class of anticancer agents. Chemical Biology & Drug Design, Oxford, Inglaterra, v. 83, n. 1, p. 126-131, 2014.
1747-0277
http://www.repositorio.ufc.br/handle/riufc/7215
identifier_str_mv RODRIGUES, F. A. R. et al. Mefloquine–Oxazolidine derivatives : a new class of anticancer agents. Chemical Biology & Drug Design, Oxford, Inglaterra, v. 83, n. 1, p. 126-131, 2014.
1747-0277
url http://www.repositorio.ufc.br/handle/riufc/7215
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv 1747-0277
publisher.none.fl_str_mv 1747-0277
dc.source.none.fl_str_mv reponame:Repositório Institucional da Universidade Federal do Ceará (UFC)
instname:Universidade Federal do Ceará (UFC)
instacron:UFC
instname_str Universidade Federal do Ceará (UFC)
instacron_str UFC
institution UFC
reponame_str Repositório Institucional da Universidade Federal do Ceará (UFC)
collection Repositório Institucional da Universidade Federal do Ceará (UFC)
repository.name.fl_str_mv Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)
repository.mail.fl_str_mv bu@ufc.br || repositorio@ufc.br
_version_ 1813028753131962368