Synthesis, X-ray crystal structure, Hirshfeld combined with DFT and anticancer efficacy of (Z)–N-methyl-C-aryl aldonitrones

Lasri J., Soliman S. M., Ali E. M., Eltayeb N. E., Dege N., Alzahrani F. A.

Journal of Molecular Structure, cilt.1313, 2024 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1313
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1016/j.molstruc.2024.138699
  • Dergi Adı: Journal of Molecular Structure
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • Anahtar Kelimeler: (Z)–N-methyl-C-aryl aldonitrones, Anticancer, DFT, Hirshfeld, X-ray single crystal
  • Ondokuz Mayıs Üniversitesi Adresli: Evet

Özet

(Z)–N-methyl-C-aryl aldonitrones –O + N(Me)=C(H)R (1 R = 2-naphthyl, 2 R = 2‑hydroxy-1-naphthyl, 3 R = 1-naphthyl, 4 R = 2-hydroxyphenyl) were synthesised and fully characterised by several methods. The supramolecular structure aspects of 1 and 2 were analysed utilizing Hirshfeld topology analysis. In 1, the most common contacts are the H…H (45.1 %), C…H (39.1 %) and O…H (13.0 %) interactions while the corresponding values in case of 2 are 47.7, 24.0 and 18.8 %, respectively. The C…H and O…H interactions have the characteristic features of short important contacts in 1 while only the O…H interaction is the most significant in case of 2. Based on DFT calculations, the HOMO, LUMO, natural charges, polarity as well as chemical reactivity descriptors were predicted and compared for both compounds. On the other hand, compounds 1–4 reduced the growth of MCF-7 and T47D. Compound 3, which has the lowest IC50 values against the MCF-7 and T47D cell lines, is thought to be the most promising applicant as an anticancer drug.