1442018-40-7Relevant academic research and scientific papers
New carbohydrate-derived S,S -dioxothiochroman derivatives and their unexpected easy epimerization at the anomeric position
Kinfe, Henok H.,Makolo, Felix L.,Moshapo, Paseka T.,Phasha, Zanele H.
, p. 193 - 204 (2013)
An efficient and stereoselective procedure is developed for high-yield preparation of novel S,S-dioxothiochroman carbohydrate derivatives 5a-e from their corresponding sulfone epimers 3a-e via anomeric epimerization in the presence of sodium hydride. Copy
Preparation and antimalarial activity of a novel class of carbohydrate-derived, fused thiochromans
Kinfe, Henok H.,Moshapo, Paseka T.,Makolo, Felix L.,Gammon, David W.,Ehlers, Martin,Schmuck, Carsten
, p. 197 - 202 (2015/02/18)
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.
