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Structure-activity relationship for antibacterial action of phenolic and aromatic nitro compounds. An attempt at systematic identification of new antibacterial agents.

A structure-activity relationship between antibacterial activity and the energy of the lowest unoccupied molecular orbital (LUMO) of phenolic and aromatic nitro compounds was derived based on results obtained with eight strains of Gram-positive and Gram-negative bacteria. The reliability of the correlation was confirmed by measuring the minimum inhibitory concentration at various pH values of the medium ; it was found that the undissociated molecular species having a low lying LUMO is essential for strong antibacterial activity. Based on the above results, 2, 4, 6-trinitroanisole was examined, and it proved to have a remarkably strong antibacterial activity (200 times stronger than that of 2, 4, 6-trinitrophenol).