Abstract
Three seco-acyclo- N - and - S - nucleosides analogues :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 in a common synthetic pathway. Treatment of (2E)-3-phenylprop-2-enehydrazide with CS 2 under different conditions led to oxadiazole and thiadiazole derivatives while when oxadiazole was reacted with hydrazine hydrate gave N-amino triazole derivative. These diazole thiols gave the nucleoside analogus when treated with freshly prepared 2-phenyl-1,3-dioxan-5-yl 4-methylbenzenesulfonate. All reaction intermediates and final products where characterized by IR, 1 H- and 13 C-NMR spectroscopy . The antibacterial activities assessed using the paper disk diffusion method against microorganism Gram-positive bacteria, Staphylococcus aureus , Bacillus ce reus , 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.
Highlights
Cis- and trans-cinnamic acid moiety is present in some important phenylpropanoid natural products such as lignins, naringenine chalcone (A), flavone (B) and coumarine (C)
Cinnamic acid derivatives have been utilized in a wide range of biological activities such as anticancer,2,3 antioxidant,3,4 anti-inflammatory,5 antibacterial,1,4,6 antifungal,7-9 antiviral,10 dietary11 and as a fragrance ingredient in many fragrance formulations
In this work we report first, the conversion of some modified cinnamic acid to 1,3,4-oxadiazolethiol, 1,3,4-thiadiazolethiol and Namino-1,2,4-triazolethiol derivatives
Summary
Three seco-acyclo-N- and -S- nucleosides analogues, namely 2-phenyl-1,3-dioxan-5-yl 5-[(E)-2-phenylethenyl]-1,3,4-oxadiazole-2sulfenate, 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-5yl)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.
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