Kinfe Henok H, Moshapo Paseka T, Makolo Felix L, Gammon David W, Ehlers Martin, Schmuck Carsten
Department of Chemistry, University of Johannesburg, Auckland Park 2006, South Africa.
Department of Chemistry, University of Johannesburg, Auckland Park 2006, South Africa.
Eur J Med Chem. 2014 Nov 24;87:197-202. doi: 10.1016/j.ejmech.2014.09.060. Epub 2014 Sep 19.
A novel class of fused thiochroman derivatives has been prepared by an efficient and versatile synthetic procedure involving nucleophilic displacement of the side-chain iodo substituent in 2-deoxy-2-C-iodomethyl glucosides by thiophenolate ions, and subsequent intramolecular C-glycoside formation. A range of aromatic substituents is tolerated, and the subsequent facile selective oxidation of the sulfur to the sulfoxide or sulfone level expands the range and molecular diversity of the series of compounds. A selection of the sulfoxide and sulfone derivatives bearing lipophilic substituents on the aromatic portion were found to have antimalarial activities in the low micromolar range.
