Abstract
A (pyridazinyl)acetate derivative was reacted with thiosemicarbazide and hydrazine hydrate to yield spiropyridazinone and acetohydrazide derivatives, respectively. The acetohydrazide derivative was used as a starting material for synthesizing some new heterocyclic compounds such as oxoindolinylidene, dimethylpyrazolyl, methylpyrazolyl, oxopyrazolyl, cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives. The behavior of the cyanoacetylacetohydrazide and oxadiazolylacetonitrile derivatives towards nitrogen and carbon nucleophiles was investigated. The assigned structures of the prepared compounds were elucidated by spectral methods (IR, 1H-NMR 13C-NMR and mass spectroscopy). Some of the newly prepared compounds were tested in vitro against a panel of four human tumor cell lines, namely hepatocellular carcinoma (liver) HePG-2, colon cancer HCT-116, human prostate cancer PC3, and mammary gland breast MCF-7. Also they were tested as antioxidants. Almost all of the tested compounds showed satisfactory activity.
Highlights
Living organisms have difficulties in the construction of N-N bonds that limits the natural abundance of compounds having such bonds
The substituents at position 2 of the pyridazinone ring do not fall into a clear pattern; alterations at this position can have major effects on the activity of the resulting compounds
Further investigations will be required for a more detailed evaluation of anticancer pyridazine compounds with different molecular mechanisms for enhancing anticancer activities and minimizing toxicities. For these reasons we have introduced hydrazide and 1,3,4-oxadiazole moieties to the pyridazine ring to enhance the cytotoxic activity
Summary
Living organisms have difficulties in the construction of N-N bonds that limits the natural abundance of compounds having such bonds. Pyridazinone derivatives, a class of compounds containing the N-N bond, exhibit a wide range of pharmacological activity [1], including analgesic, antidepressant, anti-inflammatory [2,3,4,5,6], antimicrobial [7,8] as well as herbicidal activities [9]. There are numerous reports available in the literature, which indicate the potential anticancer effects of pyridazinones. ( NSC 351478) were effective in the treatment of P388 leukemia in mice. The substituents at position 2 of the pyridazinone ring do not fall into a clear pattern; alterations at this position can have major effects on the activity of the resulting compounds. More specific was the effect of chlorinating the phenyl rings. Position 41 seems most important, but a second chlorine at position
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