The uses of ethyl 2-(1H-benzo[D]imidazol-2-yl)acetate to synthesis pyrazole, thiophene, pyridine and coumarin derivatives with antitumor activities

R M Mohareb,M S Gamaan

doi:10.4314/bcse.v32i3.13

Abstract

In the present work, the ethyl 2-(1H-benzo[d]imidazol-2-yl)acetate (3) was subjected to a series of heterocyclization reactions through its reaction with different chemical reagents. The resulting molecules were thiophene, pyrazole, coumarin derivatives incorporated benzo[d]imidazole moiety. All the synthesized compounds were determined by elemental analysis, 1H NMR, 13C NMR, and MS. The antitumor evaluations of the newly synthesized products toward the three cancer cell lines MCF-7 (breast adenocarcinoma), NCI-H460 (non-small cell lung cancer), and SF-268 (CNS cancer) showed that compounds 5a, 9b, 9c, 17, 23b and 38 were of the highest potencies among the synthesized compounds. KEY WORDS: Oxobutanamide, Thiophene, Pyrazole, Pyran, Pyridine Bull. Chem. Soc. Ethiop. 2018, 32(3), 541-557.DOI: https://dx.doi.org/10.4314/bcse.v32i3.13

Highlights

Benzimidazole derivatives have provided a large number of biologically active compounds that have been intensively used in medicinal chemistry as drugs
We synthesized a series of heterocyclic compounds derived from ethyl 2(1H-benzo[d]imidazol-2-yl)acetate together with their antitumor evaluations
The effects of the synthesized compounds on the in vitro growth of human tumor cell lines were evaluated according to the procedure adopted by the National Cancer Institute (NCI, USA) in the ‘In vitro Anticancer Drug Discovery Screen’ that uses the protein-binding dye sulforhodamine B to assess cell growth

Summary

Introduction

Benzimidazole derivatives have provided a large number of biologically active compounds that have been intensively used in medicinal chemistry as drugs. We synthesized a series of heterocyclic compounds derived from ethyl 2(1H-benzo[d]imidazol-2-yl)acetate together with their antitumor evaluations. The reaction of compound 3 with acetylacetone (16) gave the benzo[4,5]imidazo[1,2a]pyridine derivative 17.

Results

Conclusion