Journal
POLYCYCLIC AROMATIC COMPOUNDS
Volume 42, Issue 6, Pages 3523-3544Publisher
TAYLOR & FRANCIS LTD
DOI: 10.1080/10406638.2020.1870507
Keywords
3-Cyanopyridinacetohydrazide; 1,3-Dioxole-5-carbaldehyde; 1,3,4-Oxadiazoles; Cytotoxicity; Docking study
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Funding
- Faculty of Womens for Arts, Science and Education, Ain Shams University
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A series of reactions were conducted to synthesize benzohydrazide and nicotinonitrile derivatives, which were then tested for cytotoxicity against breast cancer cells. Some compounds showed lower half-maximal inhibitory concentrations, indicating potential anticancer activity.
N'-(2-((4-(Benzo[d][1, 3]dioxol-5-yl)-3-cyano-6-(naphthalen-2-yl)-pyridin-2-yl)oxy)- acetyl)benzohydrazide (6) and hydrazide derivatives (7-10) were synthesized via reaction of 3-cyano-pyridinacetohydrazide (5) with benzoylchloride and the appropriate aldehyde, respectively. Also, 4-(Benzo[d][1, 3]dioxol-5-yl)-2-(2-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethoxy)-6-(naphthalen-2-yl) nicotinonitrile (11) was prepared through reaction of (5) with ethylacetoacetate. In addition, the hydrazide 5 was used as a starting material for synthesizing other nicotinonitrile derivatives (12, 13) and acetohydrazides (14, 15). Moreover, new 2, 5-disubsitituted-1,3,4-oxadiazoles (16, 17) were furnished by the reaction of (5) with benzoic acid derivatives. The cytotoxicity for some new compounds was investigated against human breast cancer MCF-7 and MDA-MB-231 cell lines at concentrations (0, 10, 20, 40, 60, 80, and 100 mu g/ml) using MTT assay. Compounds (4, 9, 14 and 17) were recorded the lowest half-maximal inhibitory concentrations (IC50s) against MCF-7 and MDA-MB-231 cell lines via cytotoxicity assays. These results were confirmed using molecular docking experiments. From the previous observations, we suggested that our synthesized compounds could be of great potential against breast cancer cells.
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