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Synthesis and anticancer properties of novel hydrazone derivatives incorporating pyridine and isatin moieties
Author(s) -
Zebbiche Zineddine,
Tekin Suat,
Küçükbay Hasan,
Yüksel Furkan,
Boumoud Boudjemaa
Publication year - 2021
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.202000377
Subject(s) - isatin , docetaxel , chemistry , hydrazone , ic50 , pyridine , stereochemistry , nuclear chemistry , medicinal chemistry , organic chemistry , in vitro , biochemistry , biology , genetics , chemotherapy
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 1 H nuclear magnetic resonance (NMR), 13 C NMR, and Fourier‐transform infrared spectroscopic techniques and elemental analysis. Cell viability assays for the tested hydrazone derivatives were performed and the log IC 50 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 IC 50 value of 0.2200 μM ( 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 IC 50 of docetaxel was 0.2200 μM for A‐2780 cells at 24 h, the IC 50 values of these compounds were −0.4987, −0.4044, −0.8138, −0.3868, −0.6954, −0.4751, and 0.1809 μM, 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 IC 50 of docetaxel was 0.2400 μM for MCF‐7 cells at 24 h, the log IC 50 values of compounds 4b , 4d , and 4i were −0.1293, −0.1700, and 0.2459 μM, respectively.