化学療法剤の研究(第7報) : ニトロイミダゾール誘導体の合成研究その2 4(or 5)-Nitro-5(or 4)-styrylimidazole誘導体および4(or 5)-(β-Phenyl-β-hydroxy)-ethyl-5(or 4)-nitroimidazole誘導体の合成と抗微生物作用

概要

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2-Methyl-4(or 5)-substitutedstyryl-5(or 4) nitroimidazole (X), 1,2-dimethyl-4-substitutedstyryl-5 (or 4)-nitroimidazole (XI), and 1,2-dimethyl-4-nitro-5-substitutedstyryl imidazole (XII) were prepared respectively by the reaction of 2,4(or 5)-dimethyl-5(or 4)-nitroimidazole (IV), 1,2,4-trimethyl-5-nitroimidazole (V), and 1,2,5-trimethyl-4-nitroimidazole (VI) with benzaldehyde derivatives (X) in the presence of piperidine (Table I, II and III). 1,2-Dimethyl-4-nitro-5-[(β-hydroxy-β-phenyl) ethyl] imidazole (XIII), 1-benzyl-2-methyl-4-nitro-5-[(β-hydroxy-β-phenyl) ethyl] imidazole (XIV), and 1-β-hydroxyethyl-2-methyl-4-nitro-5-[(β-hydroxy-β-phenyl) ethyl]i midazole (XV) were prepared respectively by the reaction of VI, 1-benzyl-2,5-dimethyl-4-nitroimidazole (VII), and 1-β-hydroxyethyl-2,4-dimethyl-5-nitroimidazole (VIII) with X in the presence of sodium ethoxide (Table IV, V and VI). 1-Methyl-2,4-bis [β-(2-furyl) vinyl]-5-nitroimidazole was obtained by the reaction of V with furfural (XVI) and 1,2-dimethyl-4-nitro-5-[2'-furyl-3'-(1", 2"-dimethyl-4"-nitro-5"-imidazolyl) propyl] imidazole (XVIII) was obtained by the reaction of VI with XVI. Antimicrobial activity of their derivatives in vitro was examined and the results are listed in Table VII.
社団法人日本薬学会の論文
1971-02-25