Synthesis, biological evaluation and molecular docking studies of a new series of bis-chalcones

• Published in: Research on chemical intermediates Vol. 49; no. 1; pp. 273 - 287
• Main Authors: Khazaei-Poul, Zahra, Mahmoodi, Nosrat Ollah, Taherpour Nahzomi, Hossein
• Format: Journal Article
• Language: English
• Published: Dordrecht Springer Netherlands 2023; Springer Nature; Springer Nature B.V
• Subjects: Antioxidants; Ascorbic acid; Benzaldehyde; Binding; Catalysis; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry, Multidisciplinary; Claisen-Schmidt reaction; Condensates; Inorganic Chemistry; Ketones; Molecular docking; Physical Chemistry; Physical Sciences; Scavenging; Science & Technology; Xanthine oxidase; Tubulin inhibitor; Synthesis; hydroxychalcones; Molecular modeling; TARGET; DESIGN; COLCHICINE; PROTEIN; Bis-hydroxychalcones; AGENTS; INHIBITORS; DERIVATIVES; DISCOVERY
• ISSN: 0922-6168; 1568-5675
• DOI: 10.1007/s11164-022-04872-w

A convenient and efficient reaction for the synthesis of several new bis -hydroxy derivatives of chalcones 4a–h was accomplished via the two-directional Claisen–Schmidt condensation of different ketones 3a–e with premade benzaldehyde 2 under alkaline conditions. Products were obtained with reasonable yields and with excellent purity. The in vitro antioxidant activity of bis -hydroxychalcones was assessed by DPPH radical scavenging activity in comparison with ascorbic acid, and products showed good antioxidant activity. To determine the possible binding mechanisms with the active site of tubulin and bovine xanthine oxidase (BXO), docking analyses were performed. According to the docking results, compounds 4b and 4a showed the best binding affinity of − 9.13 and − 9.11 kcal/mol for tubulin, respectively. Furthermore, as before, the greatest scores for the case of BXO belong to 4b and 4a with the scores of the values − 10.32 and − 9.81 kcal/mol. Graphical Abstract