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

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.

Bibliographic Details

Main Authors:	Casellato,Annelise, Neves,Amanda P., Carneiro,J. Walkimar de M., Vargas,Maria D., Visentin,Lorenzo do C., Magalhães,Alviclér, Câmara,Celso A., Pessoa,Claudia, Costa-Lotufo,Letícia V., Marinho Filho,José D. B., Moraes,Manoel O. de
Format:	Digital revista
Language:	English
Published:	Sociedade Brasileira de Química 2010
Online Access:	http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532010000100024
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