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Nucleosides Nucleotides Nucleic Acids. 2012;31(11):783-800. doi: 10.1080/15257770.2012.732250.

Synthesis and antimicrobial evaluation of novel pyrazolones and pyrazolone nucleosides.

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  • 1Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt. abdallaelsayed@zu.edu.eg

Abstract

The synthesis of a novel series of 4-arylhydrazono-5-methyl-1,2-dihydropyrazol-3-ones 4a-h, and their N (2)-alkyl and acyclo, glucopyranosyl, and ribofuranosyl derivatives is described. K(2)CO(3) catalyzed alkylation of 4a-h with allyl bromide, propargyl bromide, 4-bromobutyl acetate, 2-acetoxyethoxymethyl bromide, and 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide proceeded selectively at the N (2)-position of the pyrazolinone ring. Glycosylation of 4a with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose under Vorbruggen glycosylation conditions gave the corresponding N (2)-4-arylhydrazonopyrazolone ribofuranoside 9a in good yield. Conventional deprotection of the acetyl protected nucleosides furnished the corresponding 4-arylhydrazonopyrazolone nucleosides in good yields. Selected numbers of the newly synthesized compounds were screened for antimicrobial activity. Compounds 4b, 12a, and 14 d showed moderate activities against Aspergillus flavus, Penicillium sp., and Escherichia coli.

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