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

Journal of the Brazilian Chemical Society

Annelise Casellato²  Amanda P. Neves²  J. Walkimar De M. Carneiro²  Maria D. Vargas²  Lorenzo Do C. Visentin¹  Alviclér Magalhães¹  Celso A. Câmara¹  Claudia Pessoa¹  Letícia V. Costa-lotufo¹  José D. B. Marinho Filho¹  Manoel O. De Moraes¹ 

[1] ,Universidade Federal Fluminense Instituto de Química Niterói RJ ,Brazil

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

DOI  :  10.1590/S0103-50532010000100024

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】

CC BY   
 All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License