Green synthesis of 2,4-dinitro-substituted bischalcones using bifunctional magnetic nanocatalyst

Article type: Research Article

Authors: Doroudi, Alireza^{a; b} | Saeidi Rashk Oliaei, Raziye^c | Khorsandi, Layasadat^d | Tahmasebi Birgani, Mohammad Javad^e | Zarei Ahmady, Amanollah^{f; *}

Affiliations: [a] Nanotechnology Research Center, Ahvaz Jundishapur University of Medical Sciences, Ahvaz, Iran | [b] Drug Discovery and Development Research Group, College of Pharmacy and Nutrition, University of Saskatchewan, Saskatoon, Canada | [c] Department of Medicinal Chemistry, School of Pharmacy, Ahvaz Jundishapur University of Medical Sciences, Ahvaz, Iran | [d] Cellular and Molecular Research Center, Medical Basic Sciences Research Institute, Ahvaz Jundishapur University of Medical Sciences, Ahvaz, Iran | [e] Department of Radiation Therapy, Golestan Hospital, Ahvaz Jundishapur University of Medical Sciences, Ahvaz, Iran | [f] Marine Pharmaceutical Science Research Center, Ahvaz Jundishapur University of Medical Sciences, Ahvaz, Iran

Correspondence: [*] Corresponding author: Amanollah Zarei Ahmady, Marine Pharmaceutical Science Research Center, Ahvaz Jundishapur University of Medical Sciences, Ahvaz, Iran. Tel.: +98 61 33361969; E-mail: zarei-a@ajums.ac.ir; ORCID Number: 0000-0001-9315-9149.

Abstract: Flavonoids have many biological properties, such as anticancer activity. Chalcones, one of their subunits, attribute their biological activity to their enone part. The presence of dinitrophenyl group in bischalcone because of its radiosensitivity property is important. Radiosensitivity property reduces radiation time in cancer patients and reduces damage to their healthy tissues. In this regard, 2,4-dinitrophenyl bischalcones were synthesized. The presence of 2,4-dinitrobenzaldehyde as a fixed component in synthesis pathway, leads to a reduction in yield of synthesis by common catalysts. Therefore, in this study, for bis-chalone synthesis, we used Graphene Oxide/Fe3O4/L-Proline nanocomposite as a green recoverable bifunctional organocatalyst. This catalyst was recovered simply by applying an external magnet and reused for eight runs. In this research, chalcones and asymmetric bis-chalcones have been synthesized with diverse substitutes in high yields (78–97%). Also, short reaction times (10–82 min), and simple experimental procedures with easy work-up are advantages of the introduced procedure. The synthesized compounds were characterized by melting point and analytical techniques. The chemical structures of synthesized compounds were confirmed by means of IR, 1HNMR, and 13CNMR.

Keywords: Magnetic Catalyst, α, β-unsaturated ketones, asymmetric bischalcones, 2, 4-dinitrobenzaldehyde, Claisen–Schmidt condensation, radiosensitivity

DOI: 10.3233/MGC-220085

Journal: Main Group Chemistry, vol. 22, no. 4, pp. 485-496, 2023