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

Journal of the Brazilian Chemical Society

Marinho Filho, José D. B.¹  Moraes, Manoel O. de¹  Câmara, Celso A.¹  Universidade Federal Rural de Pernambuco, Recife, Brazil¹  Carneiro, J. Walkimar de M.¹  Visentin, Lorenzo do C.¹  Universidade Estadual de Campinas, Campinas, Brazil¹  Casellato, Annelise¹  Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil¹  Universidade Federal do Ceará, Fortaleza, Brazil¹  Vargas, Maria D.¹  Magalhães, Alviclér¹  Costa-Lotufo, Letícia V.¹  Universidade Federal Fluminense, Niterói, Brazil¹  Neves, Amanda P.¹  Pessoa, Claudia¹ 

关键词: Nor-lapachol;    arylamine;    aminonaphthoquinone;    electrochemistry;    B3LYP;    antitumor activity;   

DOI  :  10.1590/S0103-50532010000100024

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

Novel 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.

【 授权许可】

Unknown