Synthesis and anticancer properties of novel hydrazone derivatives incorporating pyridine and isatin moieties


Zebbiche Z., TEKİN S., KÜÇÜKBAY H., Yuksel F., Boumoud B.

ARCHIV DER PHARMAZIE, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume:
  • Publication Date: 2020
  • Doi Number: 10.1002/ardp.202000377
  • Journal Name: ARCHIV DER PHARMAZIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, BIOSIS, CAB Abstracts, Chimica, EMBASE, International Pharmaceutical Abstracts, MEDLINE, Veterinary Science Database
  • Keywords: anticancer activity, hydrazone derivatives, isatin derivatives, pyridine derivatives, BENZYLIDENE-HYDRAZIDES, POTENT, ANTIBACTERIAL, LASSBIO-294, INHIBITORS, CHEMISTRY, DISCOVERY, COMPOUND, DESIGN, AGENTS
  • Inonu University Affiliated: Yes

Abstract

Nine novel hydrazone derivatives (4a-i) incorporating pyridine and isatin moieties were synthesized through one-pot, four-component heterocyclic condensation reactions. The structures of all new compounds (2a-e, 3a, 3c-e, and 4a-e) were identified by H-1 nuclear magnetic resonance (NMR), C-13 NMR, and Fourier-transform infrared spectroscopic techniques and elemental analysis. Cell viability assays for the tested hydrazone derivatives were performed and the log IC50 values of the compounds were calculated after a 24-h treatment. All hydrazide derivatives tested showed a promising antitumor activity against A-2780 cells as compared with the standard drug docetaxel with a log IC50 value of 0.2200 mu M (p < .05). Seven of the examined compounds (4b-e, 4g-i) showed high cytotoxic activity against A-2780 cells as compared with the standard drug docetaxel. Whereas the log IC50 of docetaxel was 0.2200 mu M for A-2780 cells at 24 h, the IC50 values of these compounds were -0.4987, -0.4044, -0.8138, -0.3868, -0.6954, -0.4751, and 0.1809 mu M, respectively. Three of the compounds, 4b, 4d, and 4i, showed high cytotoxic activity against MCF-7 cells as compared with docetaxel (p < .05). Whereas the log IC50 of docetaxel was 0.2400 mu M for MCF-7 cells at 24 h, the log IC50 values of compounds 4b, 4d, and 4i were -0.1293, -0.1700, and 0.2459 mu M, respectively.