54-25-1 Usage
Description
6-Azauridine, also known as AzUrd, is a pyrimidine nucleoside analog that exists as a white powder. It is a potent inhibitor of de novo pyrimidine synthesis and DNA synthesis, playing a significant role in various applications due to its ability to interfere with cellular nucleic acid formation.
Uses
Used in Antiviral Studies:
6-Azauridine is used as an antiviral agent for its ability to inhibit de novo pyrimidine synthesis and DNA synthesis. It is converted intracellularly into mono, di, and triphosphate derivatives, which incorporate into RNA and inhibit protein synthesis, making it a valuable compound in antiviral research.
Used in Anticancer Applications:
In the field of cancer research, 6-Azauridine is utilized as an antineoplastic antimetabolite. It interferes with pyrimidine biosynthesis, thereby preventing the formation of cellular nucleic acids, which is crucial for cancer cell growth and proliferation.
Used in Antipsoriatic Treatment:
6-Azauridine, particularly in its triacetate form, is effective as an antipsoriatic agent. It is used to treat skin conditions like psoriasis, where it helps to regulate the overproduction of skin cells.
Used in Cell Formation Studies:
6-Azauridine is also employed in research on cell formation, as it blocks the conversion of orotic acid into UMP, providing insights into the processes involved in cellular development and function.
Biochem/physiol Actions
6-azauridine is a prodrug, upon conversion to 6-aza-UMP, inhibits uridine monophosphate synthase (UMPS). It is a broad spectrum anti-metabolite. It interferes with pyrimidine biosynthesis and affects the cellular nucleic acid levels. It is considered as a antineoplastic metabolite. It inhibits RNA viruses like chikungunya virus, semliki forest virus, and human coronavirus. It significantly inhibits the growth of Cryptosporidium parasites.
Check Digit Verification of cas no
The CAS Registry Mumber 54-25-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 4 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 54-25:
(4*5)+(3*4)+(2*2)+(1*5)=41
41 % 10 = 1
So 54-25-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H11N3O6/c12-2-3-5(14)6(15)7(17-3)11-8(16)10-4(13)1-9-11/h1,3,5-7,12,14-15H,2H2,(H,10,13,16)
54-25-1Relevant articles and documents
New non-aromatic triazinic nucleosides : Synthesis and antiretroviral evaluation of β-ribosylamine nucleoside analogs
Depelley, Jean,Granet, Robert,Kaouadji, Mourad,Krausz, Pierre,Piekarski, Salomon,Delebassee, Sylvie,Bosgiraud, Claudine
, p. 995 - 1008 (2007/10/03)
Various 5-alkyl-6-aza-5,6-dihydrouridines and 6-(β-D-ribopyranosyl)-5-alkyl-6-aza-5,6-dihydrouracils have been synthesized. A new regioselective method is described for coupling triazinic bases to the sugar unit. Different epimers were isolated. Antiretroviral activity against Visna virus was evaluated.
2',3'-O-CARBONYL DERIVATIVES OF 6-AZAURIDINE IN THE SYNTHESIS OF ITS 5'-SUBSTITUTED AND 5'-DEOXY DERIVATIVES
Drasar, Pavel,Beranek, Jiri
, p. 2070 - 2082 (2007/10/02)
Preparation of 2',3'-O-carbonyl derivatives of 5'-deoxy-6-azauridine and 6-azauridine using 1,1'-carbonyldiimidazole has been elaborated. 5'-Chloro and 5'-bromo derivatives were prepared by treatment of the 5'-O-mesyl derivative with quarternary ammonium halides, 5'-chloro derivatives also by direct halogenation with thionyl chloride in hexamethylphosphortriamide or with tetrachloromethane, triphenyl phosphine, and dimethylformamide.Derivatives of 5'-bromo-6-azauridine were reduced with tributyltin hydride to 5'-deoxy-6-azauridine compounds. 6-Azauridine 2',3'-carbonate (IVa) and its 5'-derivatives IVc and IVe on treatment with imidazole in dimethylformamide afforded 2,2'-anhydronucleosides IIIa-IIIc.The 2,2'-anhydro-5'-deoxy compound IIIc underwent alkaline hydrolysis to 5'-deoxy-1-β-D-arabino-pentofuranosyl-6-azauracil (VIa).Treatment of 2,2'-anhydro-5'-deoxy-5'-chloro derivative IIIb with hydrogen chloride led to 2',5'-dichloro derivative If.
