Di-aryl-aldimines synthesis, crystal structure, anticancer efficacy, and molecular docking with active proteins

• Published in: Journal of molecular structure 2023-09, Vol.1287, p.135673, Article 135673
• Main Authors: Lasri, Jamal, Eltayeb, Naser E., Soliman, Saied M., Ali, Ehab M.M., Alhayyani, Sultan, Akhdhar, Abdullah, Hussien, Mostafa A.
• Format: Article
• Language: English
• Subjects: Anticancer; DFT; Di-aryl-aldimines; Molecular docking; Single crystal X-ray
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2023.135673

•Hirshfeld surface analysis of di-aryl-aldimines was studied.•Di-aryl-aldimines have an anticancer impact on both HepG2 and MCF-7.•Di-aryl-aldimines inhibit "4fm9″ which slows the proliferation of liver cancer.•Di-aryl-aldimines suppress the production of estrogen by "3eqm" in breast cancer.•The molecular docking is more consistent with the anticancer studies. The di-aryl-aldimines 3a and 3b have been synthesized, respectively, by reaction of 2‑hydroxy-1-naphthaldehyde 1a or 9-phenanthrenecarboxaldehyde 1b with 1-aminonaphthalene 2. Careful analysis of molecular packing at both qualitative and quantitative levels has been performed using Hirshfeld calculations. In both compounds, the CH…π and π-π stacking interactions are the most important. In case of 3a, the H…H, H…C and C…C contacts contributed significantly by 46.2, 36.0 and 7.0%, respectively. The corresponding values in case of 3b, are 44.4–47.7, 43.8–50.1 and 3.0–6.2%, respectively. The electronic aspects and NMR chemical shifts have been calculated using DFT. In both compounds, high correlation coefficients between the calculated and experimental chemical shifts have been obtained. Compounds 3a and 3b anticancer qualities prevent the development of cancer cells in the HepG2 liver cell line and the MCF-7 breast cell line, respectively. The development of molecular docking modules used components 3a and 3b against topoisomerase in liver cancer and aromatase cytochrome P450 in breast cancer receptor protein. Compounds 3a and 3b were found to have the largest influence on DNA structural alterations and inhibit the production of estrogen and progesterone in molecular docking studies. Di-aryl-aldimines, synthesis, crystal structure, DFT, anticancer efficacy, and molecular docking with topoisomerase and aromatase cytochrome P450 [Display omitted]