Semi-synthesis, antibacterial and antifungal activities of three novel thiazolidin-4-one by essential oil of Anethum graveolens seeds as starting material

• Published in: Journal of the Iranian Chemical Society 2018-11, Vol.15 (11), p.2423-2430
• Main Authors: Ahani, Zahra, Nikbin, Mohammad, Maghsoodlou, Malek-Taher, Farhadi-Ghalati, Farhang, Valizadeh, Jafar, Beyzaei, Hamid, Moghaddam-Manesh, Mohammadreza
• Format: Article
• Language: English
• Subjects: Analytical Chemistry; Biochemistry; Chemical synthesis; Chemistry; Chemistry and Materials Science; Esters; Fungicides; Inorganic Chemistry; NMR; Nuclear magnetic resonance; Oils & fats; Organic Chemistry; Original Paper; Physical Chemistry; Seeds
• ISSN: 1735-207X; 1735-2428
• DOI: 10.1007/s13738-018-1431-y

The three novel compounds of thiazolidin-4-one were synthesized by the reaction of essential oil of Anethum graveolens seeds (containing carvone) with thiosemicarbazide and acetylenic esters. The essential oil of A. graveolens seeds were analyzed by GC–MS after extraction that were containing high amount of carvone (37%). Carvonethiosemicarbazone was produced by the reaction of carvone with thiosemicarbazide that this compound in the reaction with acetylenic esters produced thiazolidin-4-one derivatives. The synthetic compounds 6a–c was confirmed by FT-IR, 1 H-NMR, 13 C-NMR and mass spectral data. Antimicrobial and antifungal activities of the synthetic compounds were assessed against 9 Gram-positive and 7 Gram-negative pathogenic bacteria as well as three fungal strains. The activities were reported as inhibition zone diameter, minimum inhibitory concentration, minimum bactericidal concentration and minimum fungicidal concentration values. Graphical abstract