- An improved and convenient procedure for the synthesis of 1-substituted imidazoles
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1-Protected imidazoles, such as 1-acetyl- and 1-benzoylimidazoles, react with various halides, such as benzyl, allyl, α-keto, and alkyl halides, to give 1-protected-3-substituted imidazolium salts in high yields. The resultant imidazolium salts are easily deprotected by treatment with water or alcohols to give the corresponding 1-substituted imidazoles in excellent yields. In this reaction the yields of 1-substituted imidazoles vary with the kinds of halides used and/or with the protecting groups, and the yields increase in the following order: benzyl halides≥allyl halides~α-keto halides>alkyl halides, and acetyl≥benzoyl>ethoxycarbonyl>diethoxymethyl>trimethylsilyl>tosyl.
- Kamijo,Yamamoto,Harada,Iizuka
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p. 1213 - 1221
(2007/10/02)
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- Imidazole derivatives
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Imidazole derivatives of the formula I and pharmaceutically acceptable acid addition salts thereof are provided: STR1 In the formula, R4 1- or 2-naphthyl, optionally substituted with Cl, Br, or I; 1,2,3,4-tetrahydro-6-naphthyl; 3-duryl, optionally 6-substituted by Cl, Br, I, NO2, CH3 or benzyl; mesityl, phenyl 2-, 3- or 4-substituted by OH, NH2, NO2, CH3 CONH, phenyl, phenoxy, cyclohexyl, phenylthio, benzylthio, C1 -C6 alkyl or C1 C6 alkylthio; 4-bibenzylyl; 3,4-dihydroxyphenyl, n=0, 1 or 2 and (a) R=H, alkyl having 1 to 6 carbon atoms or phenyl R1 =H, alkyl having 1 to 6 carbon atoms or phenyl one of R2 and R3 =H the other of R2 and R3 =H, OH, benzoyloxy, C2 -C7 alkanoyloxy, N-(C1 -C6 alkyl)-carbamoyloxy, N,N-[di-(C1 C6)alkyl]-carbamoyloxy, but if R2 =R3 =H then R=R1 =H, or (b) R=H, C1 -C6 alkyl, phenyl R1 =H, C1 -C6 alkyl, phenyl R2 +R3 =O, or STR2 The compounds of formula I are anti-convulsivants.
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- Synthesis and anticonvulsant activity of N-(benzoylalkyl)imidazoles and N-(ω-phenyl-ω-hydroxyalkyl)imidazoles
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A novel series of N-(benzoylalkyl)imidazoles and N-(ω-phenyl-ω-hydroxyalkyl)imidazoles was synthesized and evaluated for anticonvulsant activity in mice against maximal electroshock induced seizures. Some of the compounds showed an activity comparable to or better than phenytoin and phenobarbital. The N-[β-[4-(β-phenylethyl)phenyl]-β-hydroxyethyl]imidazole (38) was selected for further studies; preclinical toxicology and additional efficacy evaluations are in progress. Structure-activity relationships are discussed.
- Nardi,Tajana,Leonardi,Pennini,Portioli,Magistretti,Subissi
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p. 727 - 731
(2007/10/02)
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