Synthesis of a New Series of Furopyranone‐ and Furocoumarin‐Chromone Conjugates Followed by In–Vitro Cytotoxicity Activity Evaluation, and Molecular Docking Study. Issue 12 (25th March 2019)

• Record Type: Journal Article
• Authors: Meydani, Ali; Yousefi, Samira; Gharibi, Reza; Kazemi, Shima; Teimouri, Mohammad Bagher
• Is Part Of: ChemistrySelect. Volume 4:Issue 12(2019)
• Page Start: 3315
• Page End: 3324
• Publication Date: 2019-03-25
• Subjects: Chromone, Furocoumarin, Furopyranone, Isocyanide-based multicomponent reactions, In-vitro cytotoxicity, Molecular study; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201900009
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: In this work, new furopyranone‐ and furocoumarin‐chromone conjugates were successfully synthesized via the one‐pot three‐component condensation reactions of 3‐formylchromone derivatives, 4‐hydroxy‐6‐methylpyrone or 4‐hydroxycoumarin and alkyl or aryl isocyanides in refluxing toluene within 2 h. Molecular docking studies on cyclooxygenase enzymes (COX‐1, COX‐2) indicated that most derivatives have greater or moderate binding affinities than 3‐formylchromone which was used as a reference compound. Even some of the new products showed comparable binding energy towards the relative co‐crystalized ligand into COX‐1 and COX‐2. In general, all of the new products formed one to three hydrogen bonds with amino acid residues in the active site of both enzymes. Furthermore, the cytotoxicity activity of some selected compounds was investigated against human foreskin fibroblast cells (BJ) and human breast cancer cells (MDA‐MB‐231) using the MTT assay. All selected compounds exhibited significant cell growth inhibitory against cancerous cells with varied potencies when compared to 3‐formylchromone. However, they were much less toxic against normal cells. Abstract : A one‐pot synthesis of new chromone‐based furopyranone and furocoumarin compounds has been developed. Some of the synthesized furopyranone‐ and furocoumarin‐chromone conjugates have been found to show good potent anticancer activities against two different cancer cell lines. Molecular docking studies were performed on cyclooxygenase enzymes (COX‐1, COX‐2).