ChemInform Abstract: Azoles. Part 34. Nitroimidazole Derivatives and Their Antibacterial and Fungicidal Activity.

Zaprutko, Lucjusz; Wrzeciono, U.; Gajdzinski, M.; Bartkowiak, M.; Lutomski, K.; Michalska, Weronika; Pietkiewicz, K

doi:10.1002/chin.199439165

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“…The substrates were obtained according to literature methods 23,24 Table 1. Subsequently Al 2 O 3 (4.0 g) was added and the solvent was evaporated at a slightly increased temperature.…”

Section: Methodsmentioning

confidence: 99%

Regioselective Nitro Group Substitution. Synthesis of Isomeric 4-Amino-5-nitro- and 5-Amino-4-nitroimidazoles

Zaprutko¹,

Żwawiak²,

Olender³

et al. 2012

HETEROCYCLES

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On the basis of the reactions between 4,5-dinitroimidazole derivatives(1-methyl-4,5-dinitroimidazole, 1,2-dimethyl-4,5-dinitroimidazole and ethyl 2-(4,5-dinitroimidazol-1-yl)acetate) and cyclic amines (morpholine, piperidine or pyrrolidine) in mild conditions (THF or ethanolic solution), the order of nitro group substitution has been discovered for the first time. The influence of the solvent, steric effects and possibility of hydrogen bonds formation on the reaction direction has been discussed. Also, the way of formation of diamino-substitution product and interesting isomerization process is presented.for 2,4-and 2,5-dinitroimidazoles. Introduction of an electron accepting substituent at position 5 in the 4nitroimidazole ring causes increase in cytotoxic and radiosensibiliting activity. 1 These compounds are essential especially in the treatment of diseases caused by bacteria and protozoa. The best known -Metronidazole, is effective against Bacteroides, Fusobacterium, Megasphaera, Clostridium, sometimes Peptococcus and Helicobacter pylorii. Tinidazole was found to be active against Gardnella vaginalis, Propionibacterium, Eubacterium, Campylobacter, Actinomyces and Spirochetes. Nimorazole and ornidazole have demonstrated activity against trichomoniasis. 1-4 Besides, nitroimidazoles are good radiation enhancers of hypoxic cells. From among nitroazoles, Misonidazole seems to be the best known

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“…The substrates were obtained according to literature methods 23,24 Table 1. Subsequently Al 2 O 3 (4.0 g) was added and the solvent was evaporated at a slightly increased temperature.…”

Section: Methodsmentioning

confidence: 99%