Solid-phase synthesis and spectral properties of 2-alkylthio-6H-pyrano[2,3- f]benzimidazole-6-ones: A combinatorial approach for 2-alkylthioimidazocoumarins

Aimin Song, Jinhua Zhang, Carlito B Lebrilla, Kit Lam

Research output: Contribution to journalArticle

31 Scopus citations

Abstract

The solid-phase synthesis of 2-alkylthio-6H-pyrano[2,3-f]benzimidazole-6- ones (2-alkylthioimidazocoumarins) is described. 7-Fluoro-4-methyl-6-nitro-2- oxo-2H-1-benzopyran-3-carboxylic acid was coupled to Rink amide resin via its carboxyl group. The resin-bound scaffold then underwent aromatic nucleophilic substitution with primary amines, followed by reduction of the nitro group with tin (II) chloride. Subsequent cyclization of the o-dianilino intermediates with thiocarbonyldiimidazole (TCD) afforded resin-bound 1,3-dihydro-2-thioxo-6H- pyrano[2,3-f]benzimidazole-6-ones, which were then S-alkylated with alkyl halides in the presence of N,N-diisopropylethylamine (DIEA). The desired products were obtained in good yield with high purity after trifluoroacetic acid cleavage. The unique spectral properties of 2-alkylthioimidazocoumarins indicate that they may be useful in photodynamic therapy.

Original languageEnglish (US)
Pages (from-to)604-610
Number of pages7
JournalJournal of Combinatorial Chemistry
Volume6
Issue number4
DOIs
StatePublished - Jul 2004

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Discrete Mathematics and Combinatorics

Fingerprint Dive into the research topics of 'Solid-phase synthesis and spectral properties of 2-alkylthio-6H-pyrano[2,3- f]benzimidazole-6-ones: A combinatorial approach for 2-alkylthioimidazocoumarins'. Together they form a unique fingerprint.

  • Cite this