Crawford P W, Scamehorn R G, Hollstein U, Ryan M D, Kovacic P
Chem Biol Interact. 1986 Oct 15;60(1):67-84. doi: 10.1016/0009-2797(86)90018-9.
Cyclic voltammetry data were obtained for eight phenazines and phenazine-N-oxides, and eleven quinoxalines and quinoxaline-N-oxides: 1,6-phenazine-diol-5,10-dioxide (iodinin), iodinin copper complex, 6-methoxy-1-phenazinol-5,10-dioxide 1,6-dimethoxyphenazine-5-oxide, 1,6-phenazinediol, 1,6-dimethoxyphenazine, quinoxaline-1,4-dioxide, 2-methylquinoxaline-1,4-dioxide, 2,3-diphenylquinoxaline-1,4-dioxide, 2-carboxyquinoxaline-1,4-dioxide, 5-hydroxyquinoxaline-1,4-dioxide, 5-hydroxy-8-methoxyquinoxaline-1,4-dioxide, 2-methylquinoxaline, 2,3-diphenylquinoxaline, 5-hydroxyquinoxaline, 5-hydroxy-8-methoxyquinoxaline and 2-(2-quinoxalinylmethylene)hydrazine carboxylic acid methyl ester-1,4-dioxide (Carbadox). The di-N-oxides exhibit the most positive E1/2 values within each class. Reversible first wave reductions were observed for iodinin, iodinin copper complex, 1,6-dimethoxyphenazine-5-oxide, 1,6-dimethoxyphenazine, quinoxaline-1,4-dioxide, 2-methylquinoxaline-1,4-oxide and 2,3-diphenylquinoxaline-1,4-dioxide. The results are correlated with structure. Some relationships exist between reduction potential and reported antimicrobial activity. A possible mechanism of drug action is addressed.
获得了8种吩嗪和吩嗪 - N - 氧化物以及11种喹喔啉和喹喔啉 - N - 氧化物的循环伏安数据：1,6 - 吩嗪二醇 - 5,10 - 二氧化物（碘菌素）、碘菌素铜配合物、6 - 甲氧基 - 1 - 吩嗪醇 - 5,10 - 二氧化物、1,6 - 二甲氧基吩嗪 - 5 - 氧化物、1,6 - 吩嗪二醇、1,6 - 二甲氧基吩嗪、喹喔啉 - 1,4 - 二氧化物、2 - 甲基喹喔啉 - 1,4 - 二氧化物、2,3 - 二苯基喹喔啉 - 1,4 - 二氧化物、2 - 羧基喹喔啉 - 1,4 - 二氧化物、5 - 羟基喹喔啉 - 1,4 - 二氧化物、5 - 羟基 - 8 - 甲氧基喹喔啉 - 1,4 - 二氧化物、2 - 甲基喹喔啉、2,3 - 二苯基喹喔啉、5 - 羟基喹喔啉、5 - 羟基 - 8 - 甲氧基喹喔啉和2 - (2 - 喹喔啉基亚甲基)肼羧酸甲酯 - 1,4 - 二氧化物（卡巴氧）。二 - N - 氧化物在每类化合物中呈现出最正的E1/2值。观察到碘菌素、碘菌素铜配合物、1,6 - 二甲氧基吩嗪 - 5 - 氧化物、1,6 - 二甲氧基吩嗪、喹喔啉 - 1,4 - 二氧化物、2 - 甲基喹喔啉 - 1,4 - 氧化物和2,3 - 二苯基喹喔啉 - 1,4 - 二氧化物有可逆的第一波还原。结果与结构相关。还原电位与报道的抗菌活性之间存在一些关系。探讨了药物作用的可能机制。
