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Synthesis, characterization and biological activities of novel chalcone derivatives, containing 4, 7-ethanoisoindole-1,3-dione units

Mustafa Ceylan, İsa Karaman and Meryem Keçeci Sarıkaya

Department of Chemistry, Faculty of Arts and Science, Gaziosmanpasa University, 60250, Tokat, Türkiye

Department of Bioengineering, Faculty of Engineering and Natural Sciences, Gaziosmanpasa University, 60250, Tokat, Türkiye

Abstract: Novel chalcone derivatives, containing 4, 7-ethanoisoindole-1,3-dione units were synthesized starting from 1,3-cyclohexadine (4) and maleic anhydride (5). Addition of maleic anhydride (5) to 1,3-cyclehexadine (4) gave an endo-adduct, 3a,4,7,7a-tetrahydro-4,7-ethano-2-benzofuran-1,3-dione (6), in 90% yield. Heating the solution of the adduct dione (6) and 1-(4-aminophenyl)ethanone (7) in the presence of Et 3N in toluene at 110 oC for 24 hours afforded 2-(4-acetylphenyl)-3a,4,7,7a-tetrahydro-1H-4,7-ethanoisoindole-1,3-dione (8) in high yield. Piperidine-catalyzed addition of benzaldehyde derivatives (9a-i) to the compound 8 in CH 2Cl 2 at 55 oC gave the expected chalcone derivatives (10-i) in the range of 42% - 96% yields. The antibacterial activities of the chalcone derivatives (10a-i) were evaluated against human pathogenic microorganism and the compounds showed low activity compared to the standard, name of the standard.

Key Words: 4, 7-Ethanoisoindole-1,3-dione; chalcone; antibacterial activity; SCF.