Synthesis of dimethyl substituted benzimidazoles containing cyclopropane fused onto five to eight membered [1,2-a]alicyclic rings and influence of methyl group substituents on cytotoxicity of benzimidazolequinones

Sarah Hehir, Liz O'Donovan, Michael P. Carty, Fawaz Aldabbagh

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

Upon thermolysis 5,6-dimethyl-N-[(allyl, but-3-enyl, pent-4-enyl and hex-5-enyl-benzimidazol-2-yl)methylene]-(trans)-2,3-diphenylaziridin-1-amines (Eschenmoser hydrazones) form cyclopropane fused onto pyrrolo-, pyrido-, azepino- and azocino[1,2-a]benzimidazoles in 70, 50, 77 and 11% yield, respectively. The latter reaction also gave carbene insertion products. Dimethyl group substituents were found to significantly reduce the cytotoxicity of benzimidazolequinone towards human skin fibroblast cells.

Original languageEnglish
Pages (from-to)4196-4203
Number of pages8
JournalTetrahedron
Volume64
Issue number19
DOIs
Publication statusPublished - 5 May 2008
Externally publishedYes

Keywords

  • Antitumor agents
  • Aziridinylimines
  • Cycloaddition
  • Heterocycles

Fingerprint

Dive into the research topics of 'Synthesis of dimethyl substituted benzimidazoles containing cyclopropane fused onto five to eight membered [1,2-a]alicyclic rings and influence of methyl group substituents on cytotoxicity of benzimidazolequinones'. Together they form a unique fingerprint.

Cite this