N-2,4 -Dinitrophenyl-and N-4,5-dichloro-2-nitrophenyl-a-amino acids and esters have been synthesized in an attempt to remove the toxic effects of the nitro and dichtoronitro benzene nucleus to the host without removing antimicrobial activity. The esters were more effective than the free amino acids in reducing acute toxicity to mice. Some antibacterial and antifungal activity was retained in these derivatives, particularly the N-4,5-dichloro-2-nitrophenyl a-amino acids.
ELLENGIII and Li'?ittgens (1) have reviewed the antiinycotic arid antibacterial eBects of nitroviny-l derivatives in the benzene, thiophene, arid furan series and shown that the presence of the nitro group in these compounds generally enhanced these activities.
Other nitrocontaining furans (?), quinolines (:]), and phenols (4-6) have been tested for antibacterial action, ;ind the introduction of the nitro group has genera'lly enhanced the effectiveness of the coiny)ounds against bacteria. Serious toxic effects may be observed from the use of nitrocontaining compounds, however, such as Tien, tit al. ( ' i ) , found in a series of N-arylglycines that showed good antitubercular activity in &YO.
Previously, in this laboratory, successful use was made of D-glucamine as a detoxifying agent for ni tro-containing and halogenated benzene ilerivatives (8), but with the exception of the :!-nitrc:-3,5-dichlorophenyl residue, antibacterial ;ictivity was also removed by introduction of the ::lucamine moiety. Introduction of the glycine :and glycine ethyl ester residues into the nitro 1:)enzeries did not cause such a striking detoxication effect, but neither was the antibacterial yeclrum diminished so drastically. Since then, ..L series of N-2,4-dinitrophenyl and N-?-nitro-~,5-dic.hlorophenyl derivatives of several repre-?entative a-amino acids and their ethyl esters have been Irepared, and we now can report the effects these amino acids and esters have on the toxicities and a.ntilmcteria1 spectra of the diiiitro and tlichloronitro henzcne residues. The physical prol)erties of the compounds prepared are listed in Talile I.