Synthesis of New 3‐(Substituted Phenacyl)‐5‐[3′‐(4H‐4‐oxo‐1‐benzopyran‐2‐yl)‐benzylidene]‐2,4‐thiazolidinediones and their Antimicrobial Activity

Abstract

Synthesis of 3-(3-nitrophenacyl)thiazolidine-2,4-dione 2g and 3-(substituted phenacyl)-5-[3'-(4H-4-oxo-1-benzopyran-2-yl)-benzylidene]-2,4-thiazolidinediones 4a-g are reported in this paper. These compounds 4a-g were prepared from 3'-flavone carboxaldehyde and 3-substituted phenacyl-2,4-thiazolidinediones using Knoevenagel reaction. The structures of all compounds were confirmed by IR, 1H-NMR, mass spectral data, and elemental analyses. The molecules 4a-g were evaluated for in-vitro antimicrobial activity against Staphylococcus aureus, Candida albicans, Candida krusei, Candida glabrata, and Candida parapsilosis. Compounds 4c and 4f showed better inhibitory activity when compared to fluconazole against Candida krusei and Candida glabrata.

Synthesis, characterization and antimicrobial activity evaluation of new imidazo [2,1-b][1,3,4]thiadiazole derivatives

“…2,4-Thiazolidinedione derivatives constitute an important class of heterocyclic compounds for which diverse biological properties such as antibacterial and antifungal [21][22][23][24], antidiabetic [25], cardiotonic [26], anti-oedematus and analgesic [27], cyclooxygenase and lipoxygenase inhibitory [28] activities have been documented along past decades.…”

Synthesis and antimicrobial activity of new tetrahydro‐naphthalene‐thiazolidinedione and thiohydantoine derivatives

“…All starting materials and reagents were high‐grade commercial products purchased from Aldrich, Merck or Fluka. Compound 2a , 2c , 2e [16], 2b [17], 2d [18], 2f , 2g [19], and retinoidal‐carboxaldehyde 1 [20] were prepared according to the literature.…”

“…The reaction mixture was heated to 140–150°C for a period of 4‐6 h. The resulting precipitate was filtered, washed with H 2 O, and then with acetone. The residue was purified by column chromatography silica gel 60 (230–400 mesh ASTM) using n ‐hexane: CHCl 3 (2:1) mL or n ‐hexane: EtOAc (3:1) mL as eluant [18].…”

Design, Synthesis, and Biological Evaluation of Thiazolidine‐2,4‐dione Conjugates as PPAR‐γ Agonists

“…2,4‐Thiazolidinediones (TZDs) are an important class of compounds that enhance insulin action (insulin sensitizers) and promote glucose utilization in peripheral tissue . The chemistry of TZDs has attracted attention as they have been found to reveal several biological activities , such as antihyperglycemic , anti‐inflammatory , antimalarial , antioxidant , antitumor , cytotoxic , antimicrobial , and antiproliferative . Unlike sulfonylurea and biguanides which lead to severe hypoglycemia, TZDs are not associated with such hypoglycemic incidents.…”