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Synthesis of novel benzofuran and related benzimidazole derivatives for evaluation ofin vitro anti-HIV-1, anticancer and antimicrobial activities


Previously, we synthesized and evaluated several benzofuran derivatives containing heterocyclic ring substituents linked to the benzofuran nucleus at C-2 by a two- to four-atom spacer as potential anti-HIV-1, anticancer and antimicrobial agents. Among these derivatives,NSC 725612 andNSC 725716 exhibited interesting anti-HIV-1 activity. To further investigate the structure-activity relationship, we synthesized several new benzofuran derivatives derived from 2-acetylbenzofuran (2, 3a-c) and 2-bromoacetylbenzofuran (6; 7a,b; 8a,b). The compounds were designed to comprise the heterocyclic substituents directly linked to the benzofuran nucleus at C-2. Moreover, various related benzimidazoles derived from 2-acetylbenzimidazole and from 2-cyanomethylbenzimidazole (12a,b; 13a,b; 15; 16a,b) were also prepared as isosteres. The synthesized compounds were preliminarily evaluated for theirin vitro anti-HIV-1, anticancer and antimicrobial activity. Compounds2, 3a, 3b, and12b showed weak anti-HIV-1 activity. Compound6 exhibited mild activity againstS. aureus, while compound15 had mild activity towardsS. aureus andC. albicans. However, no significant anticancer activity was observed with any of the tested compounds. From these results, we conclude that the presence of the spacer between the heterocyclic substituent and the benzofuran nucleus may be essential for the biological activity.

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Correspondence to Soad A. M. El-Hawash.

Additional information

This work was presented in part at the Second International Conference of Pharmaceutical and Drug Industries Division Poster P. 162, 7–9 March 2005.

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Rida, S.M., El-Hawash, S.A.M., Fahmy, H.T.Y. et al. Synthesis of novel benzofuran and related benzimidazole derivatives for evaluation ofin vitro anti-HIV-1, anticancer and antimicrobial activities. Arch Pharm Res 29, 826–833 (2006). https://doi.org/10.1007/BF02973901

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Key words

  • 2-Acetylbenzofuran
  • Thiazolo[2,3-c]-1,2,4-triazoles
  • 2-Acety-1H-benzimidazole
  • Benzo[4,5]imidazo[1,2-a]pyridines
  • Anticancer
  • Anti-HIV-1
  • Antibacterial
  • Antifungal activities