59221-06-6Relevant articles and documents
Non-ATP competitive glycogen synthase kinase 3β (GSK-3β) inhibitors: Study of structural requirements for thiadiazolidinone derivatives
Castro, Ana,Encinas, Arantxa,Gil, Carmen,Braese, Stefan,Porcal, Williams,Perez, Concepcion,Moreno, Francisco J.,Martinez, Ana
, p. 495 - 510 (2008/04/05)
The 2,4-disubstituted thiadiazolidinones (TDZD) were described as the first non-ATP competitive GSK-3β inhibitors. New modifications in this heterocyclic ring are here reported to study the influence on the biological activity. The basic skeleton of 1,2,4-thiadiazole and also one of the carbonyl groups are kept, while different modifications are introduced in positions 3 and 5, respectively. The GSK-3β activity of the new thiadiazole derivatives here synthesized showed IC50 values for some of the compounds in the micromolar range. Additionally, ATP competition studies have been carried out, showing that as well as the first generation of TDZD, these new compounds act in a non-competitive manner. With this study, additional requirements for the biological activity of the TDZD family have been delineated.
Improved synthesis, antibacterial activity and potential carcinogenicity of 5-amino-1,2,4-thiadiazol-3(2H)-one
Piskala,Vachalkova,Masojidkova,Horvathova,Ovesna,Paces,Novotny, Ladislav
, p. 756 - 762 (2007/10/03)
This paper reports on the preparation of 5-amino-1,2,4-thiadiazol-3(2H)- one, a sulfur-containing analogue of cytosine with the -CH=CH- group between the positions 5 and 6 of the pyrimidine ring-replaced by the divalent sulfur (-S-). Improved procedures for the preparation of thiobiuret, some of its methyl derivatives and 5-amino-1,2,4-thiadiazol-3(2H)-one are documented. Thiobiuret and its N-methyl derivatives were obtained by addition of hydrogen sulfide to the respective 1-cyanoureas. Subsequent oxidation of thiobiuret with hydrogen peroxide in alkaline medium produced 5-amino-1,2,4-thiadiazol-3(2H)-one. This substance was traced back converted to the starting thiobiuret by reaction with cysteine hydrochloride. Alkaline degradation of thiadiazol led to the formation of 1-cyanourea isolated as its silver salt. An investigation of the thiadiazol biological activities has shown that it inhibits the growth of E. coli by 10% at 8.5 μM concentrations, but exhibited no cytostatic activity in L1210, HeLa S3 and HL-60 cell lines. Potential carcinogenicity of the prepared compounds was determined by a DC polarographic method. While the values of the parameter of carcinogenicity for all intermediates indicate only marginal carcinogenic potential, the value of the parameter of carcinogenicity for the thiadiazole indicates possible carcinogenicity of this compound.
1,2,4-Thiadiazolidine-3,5-dione
-
, (2008/06/13)
Compounds of the structure STR1 wherein Y is O, NH or NAc; X is H, β-D-ribofuranosyl or 2,3,5-tri-O-Ac-β-D-ribofuranosyl and Ac is acetyl; are useful as antimicrobal agent.