Journal: |
NUCLEOSIDES NUCLEOTIDES \& NUCLEIC ACIDS
TAYLOR \& FRANCIS INC
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Volume: |
31
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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. K2CO3 catalyzed alkylation of 4a-h with allyl bromide, propargyl bromide, 4-bromobutyl acetate, 2-acetoxyethoxymethyl bromide, and 2,3,4,6-tetra-O-acetyl-a-D-glucopyranosyl bromide proceeded selectively at the N-2-position of the pyrazolinone ring. Glycosylation of 4a with 1,2,3,5-tetra-Oacetyl- beta-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 14d showed moderate activities against Aspergillus flavus, Penicillium sp., and Escherichia coli.
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