Abstract
Methylbenzimidazole 1 is converted to imidazole acrylic acid 3 via cyclo condensation with chloral followed by hydrolysis. Compound 3 also obtained from the reaction of o -phenylenediamine with maleic anhydride. Treatment of 1 with SeO 2 yielded the oxidized product 4 (Aldehyde 4) which undergoes Wittig reaction using ester and Ph 3 P to furnish the acrylates 5. Compound 5 is also obtained by cyclocondensation of o -phenylenediamine and the corresponding maleate. Cyclization of 3 using Ac 2 O provides pyrroloimidazole 6. Imidazole 6 undergoes several transformations using HCl, ammonium hydroxide in neutral medium, o -phenylene diamine/HCl to provide acrylic acid 3, amide 7 and/or bicompound 8 respectively. Anilide 9 is obtained as a result of condensation of 3 with amines. Ester 5 undergoes 1,4-addition to benzimidazole ring to give the corresponding anilino derivative 10. Pyridazine cyclization is acheived by treatment of 5 with NH 2 OH in acidic medium. In vitro cytotoxicity is evaluated using SRB (sulphorhodamine-B) assay against two human cell lines, breast and liver carcinoma cell lines. The results show that compound 11 has strong activity against all cell lines tested.
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