Synthesis and Characterization of New Heterocyclic Compounds and Ring Fused and Evaluation of Activities as Anti-Bacterial and Anti-Cancer

Abstract

  This research included the synthesis and characterization of some new heterocyclic compound derivatives of)  triazole and thiazole) , were synthesized from the imidazole derivative 4,5-dichlorimidazole. The azo derivative (1) was prepared in the first step of this study by reacting the amino derivative (4-amino-3-nitro benzoic acid) in an acidic solution to produce diazonium salt; This molecule was then conjugated to the component (4,5-dichloroimidazole) in the basic intermediate of the derivative. Compound (1) was used to prepare the chemical acid chloride derivative (2) from the reaction. A mixture containing thionyl chloride SOCl₂. Next, the pyridine-containing thiosemicarbazide and the acid chloride derivative (2) are mixed to form derivative (3) . Reflexing this derivative in a basic media to get the triazole derivative (4) was the final step. The next step involved a ring-closure reaction between glacial acetic acid and acetic anhydride to produce the conjugated thiazole derivative (5). The (5) derivative was reacted with aromatic aldehydes(4-chlorobenzaldehyde,3,4-dimethoxybenzaldehyde,2-hydroxy-4-methoxy   benzaldehyde, 2,4-dimethoxybenzaldehyde, 3-aminobenzaldehyde, 4-hydroxy-3-nitrobenzaldehyde, 1H-indole-3-carbaldehyde) in an acidic solution that contained acetic anhydride and glacial acetic acid to create thiazolidinone derivatives (6-12). The inquiry also included measurements of the melting points and analyses of all synthesized compounds using infrared spectroscopy ,¹³CNMR and ¹HNMR. Additionally, several biological studies were carried out, The prepared compounds showed high activity against Staphylococcus aureus bacteria, which are (1, 2, 3, 4, 9, 10, 12). As for Escherichia coli bacteria, compounds (2,3,4,7,10,11,12) showed high effectiveness. When measured as antioxidants, compound 10 showed the highest inhibitory activity at 75%, followed by compound 12 at 67%. It can be concluded from the values obtained that the prepared compounds have a good ability to inhibit free radicals, so the prepared compounds are considered to have antioxidant properties. The prepared compound 10 showed good toxic effect against liver cancer cell line. This effect is due to the fact that the prepared compound contains in its structure an imidazole ring which has high biological activity and resistance to cancer, and it also contains other heterogeneous rings such as triazole which may affect certain receptors present on the surfaces of cells.