A number of 1-methyl-1H-imidazole derivatives and some of their oxygenated products were synthesized. An HPTLC technique for following the oxidation reactions in the different experimental conditions used was applied. The X-ray crystal structures of 1-methyl-2-methylsulfanyl-5-nitro-1H-imidazole, 2-methanesulfinyl-1-methyl-5-nitro-1H-imidazole and 2-methanesulfonyl-1-methyl-5-nitro-1H-imidazole were determined. The compounds obtained were investigated for antimycotic and genotoxic activities. The compounds tested were found to exert very low growth inhibition against yeasts and moulds. Moderate antifungal properties against dermatophytes were demonstrated for 5-nitro derivatives. 2-Methanesulfonyl-1-methyl-5-nitro-1H-imidazole was the most active substance. All 5-nitroimidazoles were genotoxic in Bacillus subtilis rec-assay, Salmonella microsome test and in Saccharomyces cerevisiae mitotic segregation assay. Structure-activity relationships are discussed
Synthesis, characterization, crystallographic analysis, antifungal and genotoxic properties of some 1-methyl-1H-imidazoles / Zani, F; Mazza, P; Benvenuti, Stefania; Severi, F; Malmusi, L; Vampa, Gabriella; Antolini, L.. - In: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0223-5234. - STAMPA. - 30:(1995), pp. 729-740.
Synthesis, characterization, crystallographic analysis, antifungal and genotoxic properties of some 1-methyl-1H-imidazoles
BENVENUTI, Stefania;VAMPA, Gabriella;
1995
Abstract
A number of 1-methyl-1H-imidazole derivatives and some of their oxygenated products were synthesized. An HPTLC technique for following the oxidation reactions in the different experimental conditions used was applied. The X-ray crystal structures of 1-methyl-2-methylsulfanyl-5-nitro-1H-imidazole, 2-methanesulfinyl-1-methyl-5-nitro-1H-imidazole and 2-methanesulfonyl-1-methyl-5-nitro-1H-imidazole were determined. The compounds obtained were investigated for antimycotic and genotoxic activities. The compounds tested were found to exert very low growth inhibition against yeasts and moulds. Moderate antifungal properties against dermatophytes were demonstrated for 5-nitro derivatives. 2-Methanesulfonyl-1-methyl-5-nitro-1H-imidazole was the most active substance. All 5-nitroimidazoles were genotoxic in Bacillus subtilis rec-assay, Salmonella microsome test and in Saccharomyces cerevisiae mitotic segregation assay. Structure-activity relationships are discussed
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