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

Journal of Combinatorial Chemistry
Aimin SongKit S Lam

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.

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Citations

May 24, 2012·Chemical Reviews·Marc VendrellYoung-Tae Chang
Oct 2, 2009·Journal of Biomedicine & Biotechnology·Ming ZhuDerick Lau
Apr 22, 2009·Molecular BioSystems·Jun-Seok LeeYoung-Tae Chang
May 4, 2011·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Aliye Aslı EsenpınarMustafa Bulut

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