Ulrich Hollstein

Cyclic voltammetry of phenazines and quinoxalines including mono- and di-N-oxides. Relation to structure and antimicrobial activity

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.

An integrated concept of amebicidal action: electron transfer and oxy radicals.

Cyclic voltammetry data were obtained for most of the main categories of antiamebic agents, specifically, quinones, heterocyclic nitro compounds, metal derivatives and chelators, and iminium-type ions. The reductions (our data and literature values) were for the most part reversible, with potentials usually in the favorable range of +0.10 to -0.56 V. The drug effect is believed to result generally from the catalytic production of oxidative stress usually arising from the formation of superoxide via electron transfer. In addition, relevant literature data are provided.

A 13C NMR study of two alpha-picolines

Abstract The structures of two previously unreported alpha-picolines are assigned by 13 C NMR and the spectral parameters for these two compounds are presented and discussed. Evidence for intramolecular hydrogen bonding is presented.