5115-14-0Relevant academic research and scientific papers
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.
Syntheses and antimicrobial activities of 1-(3-benzyl-4-oxo-3,4-dihydroquinazolin-2-yl)-4-(substituted) thiosemicarbazide derivatives
Alagarsamy, Veerachamy,Solomon, Viswas Raja,Krishnamoorthy,Sulthana,Narendar
, p. 1471 - 1479 (2016/02/18)
A series of 1-(3-benzyl-4-oxo-3,4-dihydroquinazolin-2-yl)-4- (substituted) thiosemicarbazides (AS1-AS10) were obtained by the reaction of 3-benzyl-2-hydrazino-3H-quinazolin-4-one (6) with different dithiocarbamic acid methyl ester derivatives. The key intermediate, 3-benzyl-2-thioxo-2,3- dihydro-1H-quinazolin-4-one (4), was obtained by the reaction of benzyl amine (1) with carbon disulphide and sodium hydroxide in dimethyl sulphoxide to give sodium dithiocarbamate, which was methylated with dimethyl sulphate to yield the dithiocarbamic acid methyl ester 2 and condensation with methyl anthranilate (3) in ethanol yielded the desired compound (4) via the thiourea intermediate. The SH group of compound (4) was methylated in the favourable nucleophilic displacement reaction with hydrazine hydrate, which afforded 3-benzyl-2-hydrazino-3H-quinazolin-4-one (6). The IR, and 1H- and 13C-NMR spectra of these compounds showed the presence of peaks due to thiosemicarbazides, carbonyl (C=O), NH and aryl groups. The molecular ion peaks of the quinazolin-4-one moiety (m/z 144) were observed in all the mass spectra of the compounds AS1-AS10. Elemental (C, H, N) analysis satisfactorily confirmed purity and elemental composition of the synthesized compounds. All the synthesized compounds were screened for their antimicrobial activity against selective gram positive and gram negative bacteria by agar dilution method. In the present study, compounds AS8 and AS9 emerged as the most active compounds of the series.
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
CARBONIC ANHYDRASE INHIBITOR COMPRISING A DITHIOCARBAMATE
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Page/Page column 13-14, (2013/04/24)
A carbonic anhydrase inhibitor which comprises a compound of general formula: R 1RZN-CSz-M+ for use in the treatment of microbial infection, eye disease or cancer; wherein R1 and R2 are each independently selected from H or an organic substituent, or together form a ring, and optionally contain one or more heteroatoms; wherein R and R2 together comprise at least 5 carbon atoms or at least 2 carbon atoms and a heteroatom, or R2 comprises at least 4 carbon atoms; and wherein M+ comprises a monovalent cation
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.
