Liquid phase organic synthesis of 3,5-disubstituted 1,3,5-thiadiazinane-2-thione derivatives on polyethylene glycol (PEG) support

Abstract

An efficient liquid-phase synthesis of 3,5-disubstituted 1,3,5-thiadiazinane-2-thione derivatives (THTT) is described using soluble polymer support polyethylene glycol (PEG) 5000 via one-pot condensation of PEG-bound free amino acid or PEG-bound tripeptide, a dithiocarbamate and formaldehyde under mild conditions. This procedure affords the target compounds in good yields and high purity with a facile work-up procedure. This synthetic approach has also allowed the efficient preparation of new compounds endowed with two THTT rings linked through the N-3 nitrogen atoms. The structures of all synthesized compounds were unequivocally established by standard spectroscopic techniques.

Identification of novel thiadiazin derivatives as potentially selective inhibitors towards trypanothione reductase from Trypanosoma cruzi by molecular docking using the numerical index poses ratio Pr and the binding mode analysis

“…Thiadiazines, more specifically 3,5-disubstituted thiadiazine-2-thione (THTT), have been studied by the Laboratory of Organic Synthesis (LSO) for more than 20 years [12][13][14][15][16]. Several biological studies in vitro have demonstrated the antiparasitic activity of THTT, which is related to a non-specific high cytotoxicity [12,13].…”