Synthesis, identification and evaluation of molecular docking and experimental anti-cancer and antioxidant activity of new spiro four membered ring derivatives bearing 5-nitro isatin

• Published in: Natural product research Vol. 38; no. 15; pp. 2629 - 2636
• Main Authors: Rasheed, Hala Ayad Mohamed, Al-Majidi, Suaad M. H.
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 02.08.2024; Taylor & Francis Ltd
• Subjects: 1,3-diazitidine-2-one; 2-thio-1,3-diazitidine; 5-nitro isatin; Anticancer properties; Antineoplastic Agents - chemical synthesis; Antineoplastic Agents - chemistry; Antineoplastic Agents - pharmacology; Antineoplastic drugs; antioxidant; Antioxidants; Antioxidants - chemical synthesis; Antioxidants - chemistry; Antioxidants - pharmacology; Biological activity; breast cancer; Chemical synthesis; Cycloaddition; Cytotoxicity; Drug Screening Assays, Antitumor; Humans; Imines; Isatin - chemistry; Isatin - pharmacology; Isocyanates; MCF-7 Cells; Molecular docking; Molecular Docking Simulation; Molecular Structure; Schiff Bases - chemistry; Schiff Bases - pharmacology; Spiro Compounds - chemical synthesis; Spiro Compounds - chemistry; Spiro Compounds - pharmacology; spiro-oxindol; Structure-Activity Relationship; Tumor cell lines; β-Lactam antibiotics; 1,3-diazitidine-2-one; antioxidant; molecular docking; 2-thio-1,3-diazitidine; spiro-oxindol; breast cancer; 5-nitro isatin
• ISSN: 1478-6419; 1478-6427; 1478-6427
• DOI: 10.1080/14786419.2023.2195178

Spiro-5-nitro isatino aza-β-lactams were produced by a [2 + 2] cycloaddition of 5-nitro isatin Schiff bases [1-5] with different aromatic isocyanate and thioisocyanate. 1HNMR and 13CNMR as well as FTIR spectroscopies, were used to identify the structures of the obtained compounds. These spiro-5-nitro isatin aza- β-lactams interest to us due to their potential antioxidant and anticancer properties. The MTT assay was used to examine in vitro bioactivity testing against breast cancer (MCF-7) cell lines. From result data, compound 14 displayed IC50 values that were lower than those of the clinically used anticancer drug tamoxifen toward MCF-7 cells after 24 h while compound 9 after 48 h synthesized compounds [6-20] were evaluated for against antioxidant activity by using DPPH assay. In molecular docking, Promising compounds were used to reveal potential cytotoxic activity mechanisms.