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Synthesis, Heterocyclization and Anti-Tumour Activity Evaluation of Some Benzimidazole Derivatives


Affiliations
1 Faculty of Science, Department of Chemistry, Zagazig University, Egypt
 

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 SeO2 yielded the oxidized product 4 (Aldehyde 4) which undergoes Wittig reaction using ester and Ph3P to furnish the acrylates 5. Compound 5 is also obtained by cyclocondensation of o-phenylenediamine and the corresponding maleate. Cyclization of 3 using Ac2O 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 NH2OH 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.

Keywords

Active Methylene, Benzimidazoles, Cytotoxicity Activity, Hydrazines, Lactambenzimidazole.
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  • Synthesis, Heterocyclization and Anti-Tumour Activity Evaluation of Some Benzimidazole Derivatives

Abstract Views: 294  |  PDF Views: 113

Authors

M. F. El-Ahwany
Faculty of Science, Department of Chemistry, Zagazig University, Egypt
Mohamed H. M. Abd El-Azim
Faculty of Science, Department of Chemistry, Zagazig University, Egypt

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 SeO2 yielded the oxidized product 4 (Aldehyde 4) which undergoes Wittig reaction using ester and Ph3P to furnish the acrylates 5. Compound 5 is also obtained by cyclocondensation of o-phenylenediamine and the corresponding maleate. Cyclization of 3 using Ac2O 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 NH2OH 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.

Keywords


Active Methylene, Benzimidazoles, Cytotoxicity Activity, Hydrazines, Lactambenzimidazole.

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DOI: https://doi.org/10.18520/cs%2Fv115%2Fi2%2F310-314