Synthesis, alpha-Glucosidase Inhibition, Anticancer, DFT and Molecular Docking Investigations of Pyrazole Hydrazone Derivatives

Karrouchi K., SERT Y., Ansar M., Radi S., El Bali B., Imad R., ...Daha Fazla

POLYCYCLIC AROMATIC COMPOUNDS, cilt.43, sa.6, ss.5021-5040, 2023 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 43 Sayı: 6
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1080/10406638.2022.2097275
  • Dergi Adı: POLYCYCLIC AROMATIC COMPOUNDS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Applied Science & Technology Source, CAB Abstracts, Chemical Abstracts Core, Communication Abstracts, Food Science & Technology Abstracts, Metadex, Pollution Abstracts, Veterinary Science Database, Civil Engineering Abstracts
  • Sayfa Sayıları: ss.5021-5040
  • Anahtar Kelimeler: Pyrazole, hydrazone, DFT, anticancer, proylendopeptidase, alpha-glucosidase, molecular docking, SELF-ASSEMBLY PROCESS, BIOLOGICAL EVALUATION, CRYSTAL-STRUCTURE, CYTOTOXICITY EVALUATION, SCALE FACTORS, SCHIFF-BASES, COMPLEXES, SIMULATIONS, ANTIOXIDANT, ACETAMIDE
  • Yozgat Bozok Üniversitesi Adresli: Evet

Özet

In this work, three N'-arylidene-5-phenyl-1H-pyrazole-3-carbohydrazide (3a-3c), derivatives have been synthesized and fully characterized by IR, H-1 & C-13 NMR and ESI-MS using experimental and theoretical methods. Theoretical calculations were carried out by DFT/B3LYP method using 6-311++G(d,p) basis set. For theoretical IR, H-1 & C-13 NMR (with GIAO method), MEP, HOMO-LUMO energies analyses of compounds 3a-3c were performed over the optimized structures. All newly synthesized compounds were screened for their cytotoxicity, proylenpeptidase and alpha-glucosidase inhibitory activities. Compounds 3c showed significant anticancer activity against lung cancer cell line (H460) with the IC50 value 0.15 +/- 0.01 mu M. The other compounds exhibited prolyl endopeptidase (PEP) activity. Compounds 3a and 3c have demonstrated a potent alpha-glucosidase inhibitory activity with the IC50 value 360.4 +/- 0.7 mu M and 370.3 +/- 1.17 mu M, respectively. Furthermore, in-silico based molecular docking study was performed between the title ligands and lung cancer cell line-H460 protein: 1M17. The best affinity bond was observed between compound 3c and the protein 1M17 with an energy of -8.6 (kcal/mol), an inhibition constant of 0.496769 mu M and an active hydrogen bond to three.