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Design and Synthesis of Some Thiazolidin-4-ones Based on (7-Hydroxy-2-oxo-2H-chromen-4-yl) Acetic Acid


Čačić, Milan; Molnar, Maja; Balić, Tomislav; Draca, Nela; Rajković, Valentina
Design and Synthesis of Some Thiazolidin-4-ones Based on (7-Hydroxy-2-oxo-2H-chromen-4-yl) Acetic Acid // Molecules, 14 (2009), 7; 2501-2513 doi:10.3390/molecules14072501 (međunarodna recenzija, članak, znanstveni)


Naslov
Design and Synthesis of Some Thiazolidin-4-ones Based on (7-Hydroxy-2-oxo-2H-chromen-4-yl) Acetic Acid

Autori
Čačić, Milan ; Molnar, Maja ; Balić, Tomislav ; Draca, Nela ; Rajković, Valentina

Izvornik
Molecules (1420-3049) 14 (2009), 7; 2501-2513

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Coumarin; dihydrazides; aromatic Schiff’s bases; N-(2-aryl-4-oxo-thiazolidin- 3-yl)-2-((4-(2-aryl-4-oxo-thiazolidin-3-ylcarbamoyl)-methyl)-2-oxo-2H-chromen-7-yloxy)- acetamides; biological activity

Sažetak
(7-Hydroxy-2-oxo-2H-chromen-4-yl)-acetic acid methyl ester (1) upon reaction with ethyl bromoacetate furnishes (7-ethoxycarbonylmethoxy-2-oxo-2H-chromen-4-yl)- acetic acid methylester (2), which on treatment with 100% hydrazine hydrate yields (7-hydrazinocarbonylmethoxy-2-oxo-2H-chromen-4-yl)-acetic acid hydrazide (3). The condensation of compound 3 with different aromatic aldehydes afforded a series of [7-(arylidenehydrazinocarbonylmethoxy)-2-oxo-2H-chromen-4-yl]-acetic acid arylidenehydrazide Schiff’s bases 4a-k. Cyclo-condensation of compounds 4a-k with 2-mercaptoacetic acid in N, N-dimethylformamide in the presence of anhydrous ZnCl2 affords N-(2-aryl-4-oxothiazolidin-3-yl)-2-(4-(2-aryl-4-oxothiazolidin-3-ylcarbamoyl)-methyl)-2- oxo-2H-chromen-7-yloxy)-acetamides 5a-k. Structure elucidation of the products has been accomplished on the basis of elemental analysis, IR, 1H-NMR and 13C-NMR data. Compounds 4a-k and 5a-k will be screened for their antibacterial activity against both Gram-positive and Gram-negative bacteria and the results reported elsewhere in due course.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Prehrambena tehnologija



POVEZANOST RADA


Ustanove
Prehrambeno-tehnološki fakultet, Osijek

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus
  • MEDLINE


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