L. Iturrino, P. Navarro, M. I. Rodríguez-Franco
Sep 1, 1987
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0
Influential Citations
17
Citations
Quality indicators
Journal
European Journal of Medicinal Chemistry
Abstract
Abstract Reduction of 1-methyl- and 1-benzyl-diethylpyrazole-3,5-dicarboxylates 2a and 2b with diisobutylaluminium hydride in toluene gave 3,5-bis-(hydroxymethyl)pyrazoles 4a and 4b in very good yields. Alternatively, 4a was obtained by reduction of S,S -diethyl 1-methylpyrazole-3,5-dicarbothioate 3″ with lithium aluminium hydride in lower yield. Treatment of above diols 4a and 4b with thionyl chloride or phosphorous tribromide in dimethoxyethane gave stable 3,5-bis-(chloromethyl)- and 3,5-bis-(bromomethyl)pyrazoles 5a, 6a and 6b . All the compounds synthesized were evaluated as being cytostatic in in vitro cultures of HeLa cells and both 1-methyl- and 1-benzyl-3,5-bis-(bromomethyl)pyrazoles 6a and 6b were found to be powerful cytostatic agents. In biological tests against Trichomonas vaginalis, Entamoeba invadens and Candida albicans , 6a and 6b showed significant trichomonacide activities.