Novel 2-(R-phenyl)amino-3-(2-methylpropenyl)-[1,4]-naphthoquinones: synthesis, characterization, electrochemical behavior and antitumor activity

dc.creatorCasellato, Annelise
dc.creatorNeves, Amanda P.
dc.creatorCarneiro, J. Walkimar de M.
dc.creatorVargas, Maria D.
dc.creatorVisentin, Lorenzo do C.
dc.creatorMagalhães, Alviclér
dc.creatorCâmara, Celso A.
dc.creatorPessoa, Claudia
dc.creatorCosta-Lotufo, Letícia V.
dc.creatorMarinho Filho, José D. B.
dc.creatorMoraes, Manoel O. de
dc.date2010-01-01
dc.date2014-07-17T17:20:54Z
dc.date2015-11-26T12:28:14Z
dc.date2014-07-17T17:20:54Z
dc.date2015-11-26T12:28:14Z
dc.date.accessioned2018-03-28T21:01:36Z
dc.date.available2018-03-28T21:01:36Z
dc.identifierJournal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 21, n. 1, p. 169-178, 2010.
dc.identifier0103-5053
dc.identifierS0103-50532010000100024
dc.identifier10.1590/S0103-50532010000100024
dc.identifierhttp://dx.doi.org/10.1590/S0103-50532010000100024
dc.identifierhttp://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000100024
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/25322
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/25322
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1239093
dc.descriptionNovel 2-(R-phenyl)amino-3-(2-methyl-propenyl)-[1,4]-naphthoquinones (R = H, 4-OMe, 4-Ferrocenyl, 4-Me, 3-Me, 4-I, 3-I, 4-CN, 3-CN, 4-NO2 and 3-NO2) derived from nor-lapachol [2-hydroxy-3-(2-methylpropenyl)-1,4-naphthoquinone] were obtained in good yields. Their structures were proposed on the basis of a single crystal X-ray diffraction study (R = OMe, 2b), ¹H and 13C NMR studies and calculations using the B3LYP functional and the 6-311+G(2d,p) basis set. The half-wave potentials of the aminonaphthoquinones and ¹H NMR chemical shifts of the 3-propenyl hydrogen in 2a-k show good correlation with the substituent Hammett constants on the phenylamino ring. The antitumor assays showed promising activity for substrate methoxy-nor-lapachol 1 and the 4-ferrocenyl derivative 2c.
dc.descriptionNovas 2-(R-fenil)amino-3-(2-metilpropenil)-[1,4]-naftoquinonas (R = H, 4-OMe, 4-Ferrocenil, 4-Me, 3-Me, 4-I, 3-I, 4-CN, 3-CN, 4-NO2 e 3-NO2) derivadas do nor-lapachol [2-hidroxi-3-(2-metilpropenil)-1,4-naftoquinona] foram obtidas em bons rendimentos. A estrutura dos compostos foi proposta com base em estudos de difração de raios-X (R = OMe, 2b), dados de RMN de ¹H e 13C e cálculos teóricos utilizando o funcional B3LYP e a base 6-311+G(2d,p). Os potenciais de meia-onda das aminonaftoquinonas e o deslocamento químico do hidrogênio da cadeia 3-propenil dos compostos 2a-k mostraram boa correlação com as constantes de Hammett dos substituintes presentes no anel fenileno. A avaliação da citotoxicidade evidenciou atividade antitumoral promissora para o substrato metóxi-nor-lapachol 1 e o derivado 4-ferrocenil 2c.
dc.description169
dc.description178
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.languageen
dc.publisherSociedade Brasileira de Química
dc.relationJournal of the Brazilian Chemical Society
dc.rightsaberto
dc.sourceSciELO
dc.subjectNor-lapachol
dc.subjectarylamine
dc.subjectaminonaphthoquinone
dc.subjectelectrochemistry
dc.subjectB3LYP
dc.subjectantitumor activity
dc.titleNovel 2-(R-phenyl)amino-3-(2-methylpropenyl)-[1,4]-naphthoquinones: synthesis, characterization, electrochemical behavior and antitumor activity
dc.typeArtículos de revistas


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