New alkyl (cyclohexyl) 2-oxo-1-(prop-2-yn-1-yl)-1, 2-dihydroquinoline-4-carboxylates: Synthesis, crystal structure, spectroscopic characterization, hirshfeld surface analysis, molecular docking studies and DFT calculations

Hayani S., SERT Y., Filali Y., Benhiba F., Chahdi F. O., Laraqui F., ...Daha Fazla

JOURNAL OF MOLECULAR STRUCTURE, cilt.1227, 2021 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1227
  • Basım Tarihi: 2021
  • Doi Numarası: 10.1016/j.molstruc.2020.129520
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Anahtar Kelimeler: Quinoline, Crystal structure, Hirshfeld surface, Molecular docking, DFT, QUINOLINE DERIVATIVES, BIOLOGICAL EVALUATION, ANTIMALARIAL ACTIVITY, IN-VITRO, DESIGN, INHIBITORS, ANALOGS, ESTERS, SERIES, DISCOVERY
  • Yozgat Bozok Üniversitesi Adresli: Evet

Özet

An efficient synthesis of novel alkyl 2-oxo-1,2-dihydroquinoline-4-carboxylates (3a-3d) was developed, starting from 2-oxo-quinoline carboxylic acid la which successively undergoes esterification and alkylation reactions. The structures of all the obtained compounds were investigated and characterized by using H-1 NMR and C-13 NMR spectroscopic measurements. The molecular and crystal structures of four compounds (3a, 3b, 3c and 3d) have also been examined by single crystal X-ray crystallography. Furthermore, the experimental data and the predicted spectral data were also obtained using density functional theory (DFT) at the B3LYP/6-31G(d,p) level of theory. Also, the closest contacts between the active atoms of the four structures were identified through Hirshfeld surface analyses, molecular docking studies, and DFT calculations. The experimental results are correlated to the calculated ones and showed great compatibility. Finally, molecular docking studies are performed to investigate the binding patterns of the titled compounds with the Protein Data Bank (PDB:1M17-EGFR kinase) inhibitor targets and showed good insights on the possible interactions using the Auto-Dock Vina program. (C) 2020 Published by Elsevier B.V.