5115-14-0Relevant articles and documents
4-Aryl-2-Imino-1,3-Dithiolanes from the Room Temperature Coupling of Sodium Dithiocarbamates with Sulfonium Salts
Bresciani, Giulio,Marchetti, Fabio,Ciancaleoni, Gianluca,Pampaloni, Guido
, p. 1615 - 1622 (2021/03/03)
A series of 4-aryl-2-imino-1,3-dithiolanes was synthesized by means of a straightforward strategy starting from readily available precursors: reactions of dithiocarbamates and arylsulfonium salts, at room temperature in water/CH2Cl2 as biphasic medium, afforded the five-membered cyclic products in good yields. The reaction mechanism was investigated by DFT calculations.
Masked thiol sugars: Chemical behavior and synthetic applications of S-glycopyranosyl-N-monoalkyl dithiocarbamates
Megia-Fernandez, Alicia,De La Torre-Gonzalez, Diego,Parada-Aliste, Jose,Lopez-Jaramillo, Francisco Javier,Hernandez-Mateo, Fernando,Santoyo-Gonzalez, Francisco
, p. 620 - 631 (2014/02/14)
The chemical behavior of S-glycopyranosyl-N-monoalkyl dithiocarbamates (DTCs) as masked 1-glycosyl thiols, easily prepared by the nucleophilic displacement of 1-halo sugars with dithiocarbamate salts of primary amines, has been studied and synthetically exploited. This behavior relies on the abstraction of the proton of the carbamate functionality that allows controlled access to thiolate sugar intermediates. The basic character of the DTC salts used as reagents leads to thiolates that evolve in situ to symmetrical diglycosyldisulfides (DGDSs) when long reaction times are allowed. Alternatively, controlled unmasking of the thiolate function can be efficiently attained by treatment with an external base of isolated anomeric glycosyl DTCs, the formation of which is prevalent when using short reaction times. In this manner, a second methodology for the preparation of symmetrical DGDSs and a chemical protocol for the S-glycosylation of any electrophilic substrate are established. The applications of this last strategy for the preparation of thioglycosyl vinyl sulfones, thiodisaccharides, and S-linked homo- and heterodivalent neoglycoconjugates are described as a proof-of-concept of the great potential of the sugar DTCs in any chemical scenario in which the covalent attachment of a thiol sugar is required. The evaluation of the biological functionality of some divalent sulfurated sugar systems is also described. Copyright
Dithiocarbamates strongly inhibit carbonic anhydrases and show antiglaucoma action in vivo
Carta, Fabrizio,Aggarwal, Mayank,Maresca, Alfonso,Scozzafava, Andrea,McKenna, Robert,Masini, Emanuela,Supuran, Claudiu T.
supporting information; experimental part, p. 1721 - 1730 (2012/05/04)
A series of dithiocarbamates were prepared by reaction of primary/secondary amines with carbon disulfide in the presence of bases. These compounds were tested for the inhibition of four human (h) isoforms of the zinc enzyme carbonic anhydrase, CA (EC 4.2.1.1), hCA I, II, IX, and XII, involved in pathologies such as glaucoma (CA II and XII) or cancer (CA IX). Several low nanomolar inhibitors targeting these CAs were detected. The X-ray crystal structure of the hCA II adduct with morpholine dithiocarbamate evidenced the inhibition mechanism of these compounds, which coordinate to the metal ion through a sulfur atom from the dithiocarbamate zinc-binding function. Some dithiocarbamates showed an effective intraocular pressure lowering activity in an animal model of glucoma.
