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Abstract The designed compounds were synthesized according to the following four schemes: Scheme 1: Scheme 1 describes the synthesis of the key intermediate imidazole derivative 4 through several steps via Dacken and West reaction. Subsequently, the cross coupling of the compound 4 with appropriate benzyl bromide derivatives and oxidation of the formed S-methylene linkers on some prepared derivatives afforded compounds 5a-e, 6.<scheme 2:Scheme 2 describes the preparation of different substituted diaryl imidazole derivatives with sulfur, S-ethanone and S-acetamide linkers through coupling of compound 4 with appropriate phenacyl bromide, chloroacetanilide or halogenated benzene derivatives to obtain the desired compounds 7a,b, 8a-h, 9 and 10. <Scheme 3:Scheme 3 illustrates the preparation of the key intermediate 1,4,5-trisubstituted imidazole derivative 11, and subsequently, its cross coupling with appropriate benzyl bromide, phenacyl bromide, chloroacetanilide or halogenated benzene derivatives to afford the 1,2,4,5-tetrasubstituted imidazole derivatives 12a,b, 13, 14a-g, 15 and 16. <Scheme 4:Scheme 4 describes the synthesis of the key intermediate ester derivative 17, and subsequently, its conversion to the corresponding acid hydrazide derivative 18 via the reaction with hydrazine. Coupling the acid hydrazide 18 with different aromatic ketones and aldehyde gave the corresponding hydrazone derivatives 19a,b and 20a-e. Different acid amide derivatives 21-23 prepared by reaction of ester compound 17 with appropriate open chain or cyclic aliphatic amines. Cytotoxicity studies for the designed imidazole compounds were established on breast (4T1-Luc2, MDA-MB-231); colon (MC-38); and melanoma (B16F10) cell lines using celastrol as reference compound. |