Abstract
Ethyl (coumarin-4-oxy)acetate 1 was prepared through the reaction of 4-hydroxycoumarin with ethyl bromoacetate. Compound 1 was allowed to react with hydrazine hydrate to produce coumarin-4-oxyacetic hydrazide 2. The synthesis of N-(arylidene and alkylidene)-coumarin-4-oxyacetic hydrazones 3-20 was performed. The preparation of 2-substituted-3-[(coumarin-4-oxy) acetamido]thiazolidinones 21-26 and 2-[(coumarin-4-oxy)methyl]-4-acetyl-5-substituted-delta2-1,3,4-oxadiazolines 27-33 was performed by the reaction of the hydrazones 3, 4, 7, 9, 12, 14 with mercaptoacetic acid and the hydrazones 3, 4, 5, 7, 12, 15, 16 with acetic anhydride, respectively. The antiviral activities, cytotoxicities and structure-activity relationship (SAR) towards different microorganisms of the prepared compounds were studied.
MeSH terms
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Anti-Infective Agents / chemical synthesis
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Anti-Infective Agents / pharmacology
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Antiviral Agents / chemical synthesis
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Antiviral Agents / pharmacology
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Coumarins / chemical synthesis*
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Coumarins / pharmacology*
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Cytotoxicity Tests, Immunologic
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Egypt
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Fungi / drug effects
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Fungi / isolation & purification
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Gram-Negative Bacteria / drug effects
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Gram-Negative Bacteria / isolation & purification
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Gram-Positive Bacteria / drug effects
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Gram-Positive Bacteria / isolation & purification
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Herpesvirus 1, Human / drug effects
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Herpesvirus 1, Human / isolation & purification
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Oxadiazoles / chemical synthesis*
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Oxadiazoles / pharmacology*
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Quantitative Structure-Activity Relationship
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Thiazolidinediones / chemical synthesis*
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Thiazolidinediones / pharmacology*
Substances
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Anti-Infective Agents
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Antiviral Agents
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Coumarins
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Oxadiazoles
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Thiazolidinediones