title: Synthesis and antimicrobial evaluation of novel pyrazolones and pyrazolone nucleosides.
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.
authors.affiliation: Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt. abdallaelsayed@zu.edu.eg
authors.forename: Abdalla E A
authors.initials: AE
authors.lastname: Hassan
authors.forename: Ahmed H
authors.initials: AH
authors.lastname: Moustafa
authors.forename: Mervat M
authors.initials: MM
authors.lastname: Tolbah
authors.forename: Hussein F
authors.initials: HF
authors.lastname: Zohdy
authors.forename: Abdelfattah Z
authors.initials: AZ
authors.lastname: Haikal
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001231:Aspergillus flavus / Q000187:drug effects*; D004926:Escherichia coli / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010407:Penicillium / Q000187:drug effects*; D047069:Pyrazolones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D009705:Nucleosides; D047069:Pyrazolones