Simple and efficient synthesis of novel glycosyl thiourea derivatives as potential antitumor agents

A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur

“…The above described inherent toxicity of the ITC functional group does of course remain unchanged and thus, these compounds have to be handled with caution. Besides the aforementioned synthesis starting from amines, several other functional groups 2,44,45,[60][61][62] can be converted to ITCs, of which isocyanides, commonly used in multicomponent reactions (MCRs), [63][64][65] are particularly interesting as they are generally less toxic. 63 The sulfurization of isocyanides with elemental sulfur was previously reported in literature for a few compounds, 66,67 however this reaction was reported to proceed only at high temperatures (80 C and 130 C) 66,67 and thus, several catalysts have since been reported to allow milder reaction conditions (Scheme 1b).…”

N-Urethane-Protected Amino Alkyl Isothiocyanates: Synthesis, Isolation, Characterization, and Application to the Synthesis of Thioureidopeptides

“…The importance of the thioureido group in conferring the required potency to bioactive molecules can be seen in its insertion into many medicinally valuable compounds. Many of the substituted thioureas are active as anti-HIV, antiviral, antimicrobial, antituberculor, antitumor, antihypertensive, and anticarcinogenic agents . The high acidity of the −NH−CS−NH− protons, in correlation with strong hydrogen bonding property has been exploited in the design of self-assembling macromolecules and stabilization of secondary structures .…”

Synthesis, antimicrobial activity and molecular simulation of thiourea derivatives containing 6-carboalkoxybenzo[d]thiazole and d-glucose moieties

“…30 Glycosyl thiourea derivatives F have remarkable inhibitory activity against human lung cancer-cell lines (PG) and human liver cancer-cell lines (BEL-7402) in vitro with EC 50 from 22.8 to 76.4 mM and from 54.9 to 82.4 mM. 34 Based on the abovementioned considerations, in this work, we present an approach for the synthetic design of thiourea derivatives containing a benzo [d]thiazole ring conjugated to a D-glucose moiety (Fig. 2).…”