Synthesis, alpha-Glucosidase Inhibition, Anticancer, DFT and Molecular Docking Investigations of Pyrazole Hydrazone Derivatives
POLYCYCLIC AROMATIC COMPOUNDS, cilt.43, sa.6, ss.5021-5040, 2023 (SCI-Expanded, Scopus)
- 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.