16312-86-0Relevant articles and documents
1-Methyl-4-aryl-urazole (MAUra) labels tyrosine in proximity to ruthenium photocatalysts
Sato, Shinichi,Hatano, Kensuke,Tsushima, Michihiko,Nakamura, Hiroyuki
, p. 5871 - 5874 (2018)
We designed and synthesised peptides conjugated with proline linkers and ruthenium photocatalysts. These peptides were used as substrates to evaluate the photocatalyst-proximity dependences of candidates for tyrosine labelling reagents. The 1-methyl-4-aryl-urazole (MAUra) structure was found to be a novel tyrosyl radical trapping agent to label tyrosine residues effectively under the conditions where the ruthenium photocatalyst and tyrosine were in close proximity. Using a ruthenium photocatalyst conjugated to a carbonic anhydrase ligand, the target protein in a complex protein mixture was labelled with remarkable target selectivity by azide- or desthiobiotin-conjugated MAUra derivatives.
Sustainable synthesis routes towards urazole compounds
Vlaminck, Laetitia,Van De Voorde, Babs,Du Prez, Filip E.
, p. 5659 - 5664 (2017)
Sustainable synthesis routes towards urazoles, the precursor molecules for triazolinediones, are reported. Not only is the use of isocyanates avoided, but the applied synthetic procedures are also mostly solvent-free, high yielding and performed in an equimolar manner. Two complementary synthesis routes have been developed starting from a wide range of amines, both based on the use of diphenyl carbonate. The first method, which is particularly suitable for the synthesis of bulk urazoles, such as butyl, cyclohexyl or benzyl urazole, is performed in bulk in a one-pot fashion and generally results in yields between 87% and 96%. The second synthesis route, with yields up to 95%, focusses on the implementation of functionalities in the urazole structure and offers the possibility to generate bifunctional urazole compounds.
Urazole synthesis. Part 2: Facilitating N4 substitution
Chai, Weirui,Nguyen, Emily,Doran, Jennifer,Han, Katie,Weatherbie, Alexander,Fernandez, Daniel,Karimi, Sarah,Mynam, Ritwick,Humphrey, Caroline,Rana, Sara,Buynak, John D.
, p. 2308 - 2310 (2013/06/26)
The di-tert-butyl-di-p-nitrophenyl ester of hydrazinetetracarboxylic acid was prepared and shown to be useful in the preparation of urazoles (i.e., 1,2,4-triazolidine-3,5-diones), by reaction with a primary amine using either n-BuLi or pyridine as base, d
An efficient and general urazole synthesis
Chai, Weirui,Chang, Yuan,Buynak, John D.
, p. 3514 - 3517 (2012/08/14)
A general two-step scheme for the synthesis of N4 substituted urazoles (i.e., 1,2,4-triazolin-3,5-diones) is described. The first step involves the reaction of a primary amine with 2.5 equiv of phenyl chloroformate to produce diphenyl (N-substituted)imidodicarbonates. The second step involves the reaction of these compounds with hydrazine to produce N4 substituted urazoles. The mild reaction conditions permit synthesis of N4 oxygenated urazoles, not available via existing methodology. Bicyclic urazoles can be prepared through the subsequent reaction of these N4-protected urazoles with 2.5 equiv of NaH in DMF together with either 1,3-dibromopropane or 2-(tert-butyldimethylsilyloxy)-1,3- dibromopropane in the presence of NaI. The resultant bicyclic urazoles are observed to display varying degrees of pyrimidalization at N1 and N2, depending on substituents.
Synthesis and anti-leishmanial activity of heterocyclic betulin derivatives
Alakurtti, Sami,Heiska, Tuomo,Kiriazis, Alexandros,Sacerdoti-Sierra, Nina,Jaffe, Charles L.,Yli-Kauhaluoma, Jari
experimental part, p. 1573 - 1582 (2010/05/02)
Betulin, a naturally occurring abundant triterpene is converted in four steps to 3,28-di-O-acetyllupa-12,18-diene. When various 4-substituted urazoles were oxidized to the corresponding urazines with iodobenzene diacetate in the presence of 3,28-di-O-acetyllupa-12,18-diene, new heterocyclic betulin derivatives were produced. These betulin derivatives were examined in a microplate assay at 50 μM for their ability to inhibit the growth of Leishmania donovani axenic amastigotes, a species that causes the fatal visceral leishmaniasis. GI50 (concentration for 50% growth inhibition) values of the most effective compounds were determined and their cytotoxicity on the human macrophage cell line THP-1 evaluated. The anti-leishmanial activity on L. donovani amastigotes growing in macrophages was also examined. The heterocycloadduct between 3,28-di-O-acetyllupa-12,18-diene and 4-methylurazine was the most effective derivative with an GI50 = 8.9 μM against L. donovani amastigotes.
Novel and efficient synthesis of 4-substituted-1,2,4-triazolidine-3,5- diones from anilines
Mallakpour, Shadpour,Rafiee, Zahra
, p. 1927 - 1934 (2008/02/04)
A simple and efficient three-step synthetic procedure for the preparation of 4-substituted phenyl derivatives of 1,2,4-triazolidindiones (urazoles), starting from anilines, has been developed. In this method, aniline derivatives were reacted with 4-nitrophenyl chloroformate to provide corresponding carbamate derivatives. In the second step, semicarbazide derivatives were prepared from these carbamates by reaction with ethyl carbazate. The cyclization reaction of corresponding semicarbazides furnished 1,2,4-triazolidindiones in high yields. Copyright Taylor & Francis Group, LLC.
A novel one-pot synthesis of 4-substituted 1,2,4-triazolidine-3,5-diones
Mallakpour, Shadpour,Rafiee, Zahra
, p. 1255 - 1256 (2007/12/26)
A simple and one-pot pathway for the preparation of 4-substituted phenyl derivatives of triazolidindiones (urazoles), starting from aniline derivatives is reported. In these methods aniline derivatives were reacted with ethyl chloroformate, to give the corresponding carbamate derivatives. In the second step semicarbazide derivatives were prepared from these carbamates by reaction with ethyl carbazide. The cyclization reactions of the corresponding semicarbazides furnished triazolidindiones. All reactions were performed in one vessel without the isolation of reaction intermediates, such as carbamates and semicarbazides, and the final products were isolated in good yields. Georg Thieme Verlag Stuttgart.
Process for the production of 1,2,4-triazolidine-3,5-diones monosubstituted in the 4-position
-
, (2008/06/13)
A process for the production of 1,2,4-triazolidine-3,5-diones corresponding to the general formula I STR1 in which R1 represents a monofunctional, optionally substituted hydrocarbon radical, optionally interrupted by hetero atoms or hetero atomic groups, characterized in that hydrazodicarbonamide or 1,2,4-triazolidine-3,5-dione is reacted with a primary amine corresponding to the general formula II or a monofunctional hydrazodiacarbonamide corresponding to the formula III in which R1 is as defined for formula I, at a temperature in the range from 150° to 280° C., under pressure of from 50 mbars to 5 bars, the reaction being accompanied by the elimination of ammonia.
Triazolidine-3,5-dione/formaldehyde/amine condensates and compositions thereof
-
, (2008/06/13)
A triazolidine-3,5-dione/formaldehyde/amine condensate is disclosed of the formula STR1 in which wherein the terms R1, R2 and R5 are defined hereinafter in the specification a process for the preparation of such condensate by reaction of a triazolidine-3,5-dione with formaldehyde and a suitable nitrogen compound and the use of the condensate as a flame-proofing agent for thermoplastics, especially polyamide and as an auxiliary for modifying polymeric substances.
