Design, Synthesis, Docking, 2D‐QSAR Modelling, Anticancer and Antioxidant Evaluation of Some New Azo‐Compounds Derivatives and Investigation of Their Fluorescence Properties

• Published in: ChemistrySelect (Weinheim) Vol. 7; no. 41
• Main Authors: Hamed, Eman O., Elsayed, Doaa A., Assy, Mohamed G., Shehab, Wesam S.
• Format: Journal Article
• Language: English
• Published: 07.11.2022
• Subjects: Antimicrobial; Antioxidant; Azo-compound; Molecular docking; QSAR
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.202202534

2,2′ (2,4‐dioxopentane‐3,3‐diyl) bis(diazene‐2,1‐diyl) dibenzoic acid was produced in this work, which was derived from the coupling reaction between two moles of diazonium salt and one mole of acetylacetone in an alkaline medium. Some derivatives based on this starting material were investigated. The structures of the good yielded synthesized composites were well characterized by different spectral techniques such as IR, 1H‐ NMR, 13C‐ NMR, and mass spectrometry. Due to the outrageous spread of cancer, these compounds were tested for the cytotoxicity against human tumor cells (HEPG‐2) and (MCF‐7) as a wide spread type of cancers in Egypt. The study illustrated that compounds 11a and 11b had a very powerful effect on two separate cell lines (HEPG‐2 and MCF‐7) and compounds 8 and 6 had a strong effect. The results of anticancer were supported by molecular docking and 2D‐QSAR modeling. In addition to testing the compounds as anticancer drugs, they were examined as antioxidant by using [DPPH] technique, antimicrobial activity (gram‐positive and gram‐negative) and antifungal activity which provided satisfactory results. The fluorescence properties were tested as an analytical application for the produced substances with good results. In this article, A number of diazine and triazine molecules were synthesized by using innovative methods. All the obtained compounds were elucidated by means of IR, 1H‐ NMR, 13C‐ NMR, and mass spectra. The effect of the compounds on human cancer (HEPG‐2) and (MCF‐7) was revealed as well as studying their antioxidant, antimicrobial activity. However, the main biological activity on this protocol was as an anticancer on human cancer (HEPG‐2) and (MCF‐7), and this activity was supported by computational studies (molecular docking and 2D‐QSAR modelling (2015)). The molecular docking provides more information regarding the ways that the chemicals created can attach to the DNA‐binding domain of Topoisomerase I (PDB ID: 1RR8). The predicted IC50 of the prepared compounds was related to the predicted IC50 by using QSAR through MOE software.