BIOBASED IMIDAZOLE DERIVATIVES WITH VERSATILE BIOACTIVITIES

Abstract Imidazole is known to be a highly momentous biomolecule since it is demonstrated to possess exceptional biological properties, like antimicrobial, antifungal, inhibition of nitric oxide synthase, and cytotoxic activities. Vanillin was used as the starting material in this study, it is a natural phenolic substance, and it makes up the majority of the vanilla orchid's bean and pod. It is used as a flavoring agent and as a preservative in the pharmaceutical industry and cosmetics. This work aims to synthesize a novel natural vanillin-based imidazolone derivatives and zwitterionic vanillin-based imidazolone derivatives with alkyl sulfonate moiety starting from the natural product vanillin. Thirty new derivatives were synthesized. Various spectroscopic methods analyzed all prepared derivatives. The anticancer properties of all derivatives were evaluated against two liver cancer cell lines (Hep-3B, LX2) and cervical cancer (HeLa). Moreover, the molecular docking between some of the prepared compounds and DNA was performed. The study discovered that a few of these substances have high impact on preventing the growth of two types of cancer cells liver cancer (Hep-3B) and cervical cancer (HeLa), and compounds with the numbers (3, 4, 5, 7, 8, 9, 11, 13, 14, 17, 24, 26) shown extraordinary efficiency against these cancer cells with low viability against the normal cells. A molecular docking study showed excellent interaction of some of these derivatives with the DNA through forming strong H-bonding. Prepared compounds with the alkyl sulfonate moieties showed improvement in the anticancer efficiency. In conclusion, a new novel set of imidazoles and synthesis of imidazolone with alkyl sulfonate moiety were successfully prepared. The anticancer activities were very promising, which makes the synthesized compounds possible future drugs for the treatment of various cancers. Keywords: Hippuric acid; oxazolone; imidazolones; anticancer; Benzimidazole; Schiff.