Nitroimidazoles chemical structures

Chemical/Pharmaceutical/Other Class An antibiotic of the nitroimidazole class Chemical Structure ... 

The nitroimidazoles are antiprotozoal drugs, with antimicrobial activity. The main nitroimidazole used in human medicine is metronidazole, whereas in veterinary medicine it is dimetridazole. Ronidazole and ipronidazole have also been used. The chemical structure of these drugs is similar to that of the nitrofurans except the nitrofuran heterocyclic ring is replaced with that of the nitroimidazole ring. The chemical structures of the nitroimidazoles are shown in Figure 12.17. 

Chemical Name l-Methyl-2-(l-methylethyl)-5-nitro-lH-imidazole Common Name 2-Isopropyl-l-methyl-5-nitroimidazole Structural Formula ... 

Chemical Name N-p-Ethylmorpholino-(5)-nitroimidazole Common Name Nitrimidazine Structural Formula ... 

Chemical Name l-[2-(Ethylsulfonyl)ethyl]-2-methyl-5-nitroimidazole Common Name -Structural Formula ... 

As with pyrazoles, the introduction of the nitro group into the imidazole ring position 4(5) leads to an approximately 30 ppm lowfield shift of the tpxo-carbon signal resonance (Tables 3.6 and 3.10) [24, 321-329], Thus, the chemical shift of the carbon atom bonded to the N02 group (C-ipso) is 149.2 ppm, whereas that of neighboring carbon (C-5) is 119.8 ppm. In 1-substituted 4-nitroimidazoles (Table 3.11) the shifts of the same carbons are 146 1 and 122 2 ppm, while in 1-substituted 5-nitroimida-zoles they are 138 1 and 132 1 ppm, respectively (Table 3.12). All this may be indicative of the possible existence of 4(5)-nitroimidazole as a 4-nitro tautomer. Moreover, another support for the structure may be provided by comparison of the proton spin-spin coupling constants - J, 2J and 1/ Cl I-111) [321, 322, 330],... 

Chemical Name 2-Amino-4-[2-(1 methyl-5-nitroimidazol-2-yl)vinyl] pyrimidine Common Name Nitromidine Structural Formula ... 

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