Synthesis and biological investigations of new thiazolidinone and oxadiazoline coumarin derivatives.
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.
Abd Elhafez
Omaima Mohamed
OM
Chemistry of Natural and Microbial Products Department, National Research Centre, Dokki, Cairo. mohamed_serry@hotmail.com
El Khrisy
Ezz El Din Ahmed Mohamed
Eel D
Badria
Farid
F
Fathy
Alaa El Din Mohamed
Ael D
D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000494:pharmacology; D003374:Coumarins / Q000138:chemical synthesis* / Q000494:pharmacology*; D003601:Cytotoxicity Tests, Immunologic; D004534:Egypt; D005658:Fungi / Q000187:drug effects / Q000302:isolation & purification; D006090:Gram-Negative Bacteria / Q000187:drug effects / Q000302:isolation & purification; D006094:Gram-Positive Bacteria / Q000187:drug effects / Q000302:isolation & purification; D018259:Herpesvirus 1, Human / Q000187:drug effects / Q000302:isolation & purification; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D021281:Quantitative Structure-Activity Relationship; D045162:Thiazolidinediones / Q000138:chemical synthesis* / Q000494:pharmacology*
D000890:Anti-Infective Agents; D000998:Antiviral Agents; D003374:Coumarins; D010069:Oxadiazoles; D045162:Thiazolidinediones