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.
References
Apr 1, 1991·Chest·C M Kessler
Jan 1, 1985·Annual Review of Biochemistry·G D CiminoJ E Hearst
Feb 5, 1987·The New England Journal of Medicine·R EdelsonG Plewig
Apr 1, 1970·Analytical Biochemistry·E KaiserP I Cook
Feb 1, 1983·Mutation Research·D J KirklandP Mannisto
May 3, 1984·The New England Journal of Medicine·R S SternH L Bleich
Jul 1, 1993·Photochemistry and Photobiology·F BordinF Baccichetti
Feb 1, 1997·Transplantation Proceedings·R Dall'AmicoU Livi
Mar 31, 1999·Journal of Dermatological Science·D BetheaF P Gasparro
Apr 14, 1999·Bioorganic & Medicinal Chemistry Letters·H ZarrinmayehD R Gehlert
May 29, 2000·Current Opinion in Chemical Biology·L A Wessjohann
Feb 22, 2002·Journal of Medicinal Chemistry·Adriana ChilinFranco Bordin
May 7, 2002·Il Farmaco·Vera KlimesováJarmila Kaustová
May 15, 2002·European Journal of Medicinal Chemistry·Vera KlimesováJarmila Kaustová
May 23, 2002·Current Opinion in Chemical Biology·John Nielsen
Jul 12, 2002·Bioorganic & Medicinal Chemistry·Cristina MarzanoAdriano Guiotto
Citations
May 24, 2012·Chemical Reviews·Marc VendrellYoung-Tae Chang
Sep 14, 2012·ACS Nano·Wan-Kyu OhJyongsik Jang
Oct 2, 2009·Journal of Biomedicine & Biotechnology·Ming ZhuDerick Lau
Apr 22, 2009·Molecular BioSystems·Jun-Seok LeeYoung-Tae Chang
Apr 21, 2009·Journal of Combinatorial Chemistry·Xiang-Shan WangShu-Jiang Tu
May 4, 2011·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Aliye Aslı EsenpınarMustafa Bulut