17331-61-2

Usage

Uses

Used in Organic Synthesis:
2,4-BIS(TRIMETHYLSILYL)-6-AZAURACIL is used as a building block for the synthesis of complex organic molecules, leveraging its unique structure and reactivity to facilitate the formation of desired products.
Used in Pharmaceutical Compounds:
As a precursor, 2,4-BIS(TRIMETHYLSILYL)-6-AZAURACIL is utilized in the preparation of functionalized uracil derivatives, which are key components in the development of novel pharmaceutical agents with potential therapeutic applications.
Used in Medicinal Chemistry:
2,4-BIS(TRIMETHYLSILYL)-6-AZAURACIL is being explored for its potential role in medicinal chemistry, where it may contribute to the discovery of new drugs or the enhancement of existing ones through its unique chemical properties.
Used in Drug Discovery:
In the field of drug discovery, 2,4-BIS(TRIMETHYLSILYL)-6-AZAURACIL is studied for its potential to contribute to the identification and development of new therapeutic agents, particularly in the area of nucleoside analogs.
Used in Nucleoside Analog Synthesis:
2,4-BIS(TRIMETHYLSILYL)-6-AZAURACIL is employed as a reagent in the synthesis of nucleoside analogs, which are important in the development of antiviral and anticancer drugs, due to their ability to interfere with nucleic acid synthesis and function.

InChI:InChI=1/C9H19N3O2Si2/c1-15(2,3)13-8-7-10-12-9(11-8)14-16(4,5)6/h7H,1-6H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 461-89-2 3,5-dihydroxy-1,2,4-triazine 
• 461-89-2 6-azauracil 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 4039-32-1 lithium hexamethyldisilazane 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 206269-47-8 1-(2',3',5'-tri-O-benzoyl-β-L-ribofuranosyl)-6-azauracil 
• 1013470-68-2 2-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-1,2,4-triazin-3,5(2H,4H)-dione 
• 61959-06-6 2-(2-oxo-2-phenylethyl)-1,2,4-triazine-3,5(2H,4H)-dione 
• 61959-08-8 2-(2-oxo-2-(4-fluorophenyl)ethyl)-1,2,4-triazine-3,5(2H,4H)-dione 
• 29725-46-0 2-(tri-O-benzyl-β-D-ribofuranosyl)-2H-[1,2,4]triazine-3,5-dione 
• 2169-64-4 2',3',5'-tri-O-acetyl-6-azauridine 
• 1146632-14-5 C₂₉H₂₃N₃O₉ 
• 1234873-91-6 C₂₉H₂₃N₃O₉ 
• 105015-84-7 2-(tri-O-benzoyl-β-D-xylofuranosyl)-2H-[1,2,4]triazine-3,5-dione 
• 1146632-13-4 C₂₉H₂₃N₃O₉ 
• 31952-61-1 5-phenyl-1,2,4-triazin-3(2H)-one 
• 61959-17-9 2-(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-2H-[1,2,4]triazine-3,5-dione 
• 267667-52-7 (2R,5S)- and (2R,5R)-1-{2-[[(tert-butyldiphenylsilyl)oxy]methyl]-1,3-oxathiolan-5-yl}-1,2,4-triazine-3,5(2H,4H)-dione 

Relevant academic research and scientific papers

Synthesis and reactions of some glycosylamine derivatives of 6-azauracil nucleosides

Reaction of the silylated 6-azauracil (2) with 2-acetamido-1,3,4,6-tetra- O-acetyl-2-deoxy-D-glucose (3) gave 1-(2-acetamido-3,4,6-tri-O-acetyl-2- deoxy-β-D-glucopyranosyl)-6-azauracil (4), which gave the free nucleoside 5 on deblocking. Acetalation of 5 gave the monoacetal 6 which was oxidized into the ketone 7. Reduction of 7 gave the allo-nucleoside 9 which on hydrolysis afforded the free nucleoside 10. Alternatively, compound 10 was obtained from mesylation of 6 to give 8 followed by subsequent acetolysis and hydrolysis.

Synthesis and DNA topoisomerase-II inhibitory activity of unnatural nucleosides

The synthesis and biological activities of a number of unnatural nucleosides (23-43) is described. Nucleosides have been synthesized by SnCl 4-catalyzed condensation of amino sugar acetates and silylated modified pyrimidines. Few of the 2′-O-acetyl derivatives of the nucleosides were hydrolyzed to the respective hydroxy derivatives by treatment with methanol saturated with ammonia. The compounds were screened against Filarial DNA-topoisomerase-II but only one of the compounds (29) inhibited this enzyme at 40 μg/mL of reaction mixture.

Chitosan–silica sulfate nanohybrid: a highly efficient and green heterogeneous nanocatalyst for the regioselective synthesis of N-alkyl purine, pyrimidine and related N-heterocycles via presilylated method

Abstract: The presilylation of purine and pyrimidine nucleobases as well as other related N-heterocycles with HMDS utilizing chitosan–silica sulfate nanohybrid (CSSNH) is described. CSSNH is proved to be a useful, highly efficient and eco-friendly heterogeneous nanohybrid catalyst for silylation of nucleobases. The presilylated nucleobases then underwent the reaction with different sources of carbon electrophiles to afford the desired N-alkyl-substituted derivatives in good-to-excellent yields. CSSNH exhibits several advantageous involving ease of handling and preparation, low cost, reusability and environmental benignity. These unique properties render the CSSNH to be an ideal candidate for use in green industrial processes. Graphic abstract: [Figure not available: see fulltext.].

Efficient and selective catalytic N-Alkylation of pyrimidine by ammonium Sulfate?Hydro-thermal carbone under eco-friendly conditions

Abstract: An efficient and inexpensive method for the N-alkylation of pyrimidines using ammonium sulfate coated Hydro-Thermal-Carbone (HTC) (AS?HTC) as reused heterogeneous catalyst was developed. The catalyst was characterized by several analytical techniques such as SEM, XRD, and FTIR. The effect of various parameters was studied including catalyst loading, mole ratio, to achieve excellent selectivity and yields in 80–90%. Significantly, the present protocol offers the use of an inexpensive and environmentally friendly catalyst and simple workup. The simplicity of the procedure, excellent yield of the products, and the recyclability of the catalyst are the main advantages of this method. Graphic Abstract: Ammonium sulfate coated Hydro-Thermal-Carbone (HTC) (AS?HTC); an efficient and reused heterogeneous catalyst of the N-alkylation of pyrimidines was developed. Excellent selectivity and yields (80–90%) toward N1-alkylpyrimidines were achieved. Significantly, the present protocol offers the use of an inexpensive and environmentally friendly catalyst and simple workup.[Figure not available: see fulltext.]

HMDS/KI a simple, a cheap and efficient catalyst for the one-pot synthesis of N-functionalized pyrimidines

The syntheses of N-Alkylpyrimidine derivatives by reacting pyrimidin-2,4-diones with appropriate alkyl halide under microwave irradiation at 400 W were compared to the conventional synthesis route. These methodologies are regioselective and compatible with numerous substrates and furnish the corresponding N-alkylpyrimidines in good yields using a cheap catalyst HMDS/KI in MeCN. A comparison study between these two different modes of heating was investigated.

Synthesis and antibacterial evaluation of 6-azapyrimidines with α-methylene-γ-(4-substituted phenyl)-γ-butyrolactone pharmacophores

A series of 6-substituted 2-[(4-methylene-5- oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1, 2,4-triazine-3,5(2H,4H)-diones (5, 6) and 2,4-bis[(4-methylene- 5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl) methyl]-1,2,4-triazine-3,5(2H,4H)-diones (9, 10) were designed, synthesized, and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. The synthesis of these compounds involved the Reformatsky-type reaction between ethyl α-(bromomethyl) acrylate and the proper ketones. Among these compounds, 2-[(4-methylene-5-oxo-2-phenyl tetrahydrofuran-2-yl) methyl]- 1,2,4-triazine-3,5(2H,4H)-dione (5a) is the most active compound and shown the selective inhibition activity against Proteus vulgaris. Springer Science+Business Media, LLC 2010.

Synthesis of new oxabicyclo[3.3.0]octane nucleoside analogues with pyrimidine bases

Synthesis of new nucleosides with an oxabiciclo[3.3.0]octane fragment in the sugar moiety was performed by Vorbruggen nucleoside synthesis with silylated pyrimidine bases: 5-FU, 5-ClU, 5-BrU, C and 6-aza-U. The compounds were characterized by IR, MS, 1H-NMR and 13C-NMR spectra and tested for their antitumor activity comparatively with U-34 and 5IU-34. Our study points out that Cl-U-34, Br-U-34 and I-U-34 might be more efficient than U-34 against the multiplication of cancer cells, like Jurkat T lymphoblasts.

A procedure for facile synthesis of nucleosides using N, O-Bistrimethyl- silylacetamide in the presence of natural phosphate coated with potassium iodide

Several α-D/L-arabino and β-D/L- xylonucleosides were synthesized in good yields under mild conditions by N-glycosylation of 1-O-acetyl D/L- arabino, and xylofuranose, with silylated nucleobases (uracil, thymine and 6- azauracil) in acetonitrile using natural phosphate (NP) coated with potassium iodide in BSA as catalyst.

Silica sulfuric acid (SSA) as a highly efficient heterogeneous catalyst for persilylation of purine and pyrimidine nucleobases and other N-heterocycles using HMDS

Purine and pyrimidine nucleobases and other N-heterocycles have been silylated with HMDS in excellent yields in the presence of a catalytic amount of silica sulfuric acid (SSA) as a heterogeneous catalyst. SSA utilizes a shorter reaction time and higher yields of silylated nucleobases. SSA is reusable for several times without a decrease in reactivity or yield of silylated adducts. Copyright

1,2,4,-TRIAZIN-3,5-DIONE COMPOUNDS FOR TREATING DISORDERS THAT RESPOND TO MODULATION OF THE DOPAMINE D3 RECEPTOR

The invention relates to compounds of the formula (I), wherein A is a saturated or unsaturated hydrocarbon chain having a chain length of 4 to 6 carbon atoms, the hydrocarbon chain being unsubstituted or substituted by 1, 2 or 3 methyl groups; R1 is selected from the group consisting of hydrogen, C1-C3alkyl and fluorinated C1-C3alkyl; R2 is hydrogen, halogen, cyano, C1-C3alkyl, C1-C3alkoxy, fluorinated C1-C3alkyl or fluorinated C1-C3alkoxy; R3 is selected from the group consisting of branched C4-C6alkyl and C3-C6cycloalkyl, and R4 is C1-C6alkyl, C3-C6cycloalkyl, fluorinated C1-C3alkyl and fluorinated C3-C6cycloalkyl. and the physiologically tolerated salts of these compounds and the N-oxides thereof. The invention also relates to a pharmaceutical composition that comprises at least one compound of the formula (I) and/or at least one physiologically tolerated acid addition salt thereof, and furtherto amethod for treating disorders that respond beneficially to dopamine D3receptor antagonists or dopamine D3agonists, said method comprising administering an effective amount of at least one compound or physiologically tolerated acid addition salt of the formula (I) to a subject in need thereof.