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seco-acyclo-N- AND -S- NUCLEOSIDE ANALOGUES FROM CINNAMIC ACID: SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITY

seco-acyclo-N- AND -S- NUCLEOSIDE ANALOGUES FROM CINNAMIC ACID: SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL ACTIVITY

Author: Mostafa Rahmouni, Adil A. Othman Silaev
Abstract

Three seco-acyclo-N- and -S- nucleosides analogues, namely 2-phenyl-1,3-dioxan-5-yl 5-[(E)-2-phenylethenyl]-1,3,4-oxadiazole-2-
sulfenate, 4-[(2-phenyl-1,3-dioxan-5-yl)amino]-5-[(E)-2-phenylethenyl]-4H-1,2,4-triazole-3-thiol and 2-[(2-phenyl-1,3-dioxan-5-
yl)sulfanyl]-5-[(E)-2-phenylethenyl]-1,3,4-thiadiazole have been synthesized from cinnamic acid via a common synthetic pathway.
Treatment of (2E)-3-phenylprop-2-enehydrazide with CS2 under different conditions led to oxadiazole and thiadiazole derivatives on
oxadiazole on treatment with hydrazine hydrate gave N-aminotriazole derivative. These diazolethiols gave the nucleoside analogues when treatment with freshly prepared 2-phenyl-1,3-dioxan-5-yl 4-methylbenzenesulfonate. All reaction intermediates and final products where characterized by IR, 1H- and 13C NMR spectroscopy. The antibacterial activities assessed against Gram-positive bacteria, Staphylococcus aureus, Bacillus cereus, and Gram-negative bacteria, Escherichia coli and Pseudomonas aeruginosa. Some of the synthetic compounds showed promising activity against microorganisms under test in comparison to commercially available antibiotics Gentamycin.

Keywords: 1,3,4-Oxadiazole-5-thione; 1,2,4-triazole-5-thiol; 1,2,4-4H aminotriazole-5-thiol; cinnamic acid; synthesis; antibacterial activity, nucleoside analogues

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