4425-56-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Cyanouracil is used as a pharmaceutical intermediate for the development of anti-cancer drugs. Its unique structure and properties make it a promising candidate for the design and synthesis of novel therapeutic agents targeting various types of cancer.
Used in Medicinal Chemistry Research:
5-Cyanouracil serves as a valuable research tool in medicinal chemistry, enabling scientists to explore its potential as a precursor for the synthesis of new compounds with anti-cancer properties. Its unique chemical structure allows for the investigation of its interactions with biological targets and the development of more effective cancer treatments.
Used in Drug Synthesis:
5-Cyanouracil is used as a key building block in the synthesis of various pharmaceutical compounds, particularly those with anti-cancer activity. Its presence in the molecular structure of these compounds can enhance their therapeutic efficacy and selectivity, making it an essential component in the development of innovative cancer therapies.
Used in Biochemical Studies:
5-Cyanouracil is utilized in biochemical research to study the interactions between nucleic acids and other biomolecules. Its unique chemical properties allow researchers to investigate the role of pyrimidines in DNA and RNA structure, function, and stability, contributing to a deeper understanding of the molecular basis of life.
Used in Chemical Education:
5-Cyanouracil serves as an educational tool in chemistry and biochemistry courses, providing students with a practical example of a pyrimidine derivative and its potential applications in the field of medicinal chemistry. It helps illustrate the principles of nucleophilic substitution and condensation reactions, as well as the importance of understanding the structure-activity relationship in drug design.

InChI:InChI=1/C5H3N3O2/c6-1-3-2-7-5(10)8-4(3)9/h2H,(H2,7,8,9,10)

Upstream product

• 61679-83-2 ethyl ureidomethylene cyanoacetate 
• 16462-28-5 5-cyanocytosine 
• 1187-34-4 α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide 
• 162129-62-6 ethyl (E)-2-cyano-3-ureido-2-propenoate 
• 85690-57-9 methyl (E)-2-cyano-3-ureido-2-propenoate 
• 1187-34-4 α-Cyano-β-ethoxy-N-(ethoxycarbonyl)acrylamide 

Downstream Products

• 3177-24-0 2,4-dichloropyrimidine-5-carbonitrile 
• 1350660-72-8 5-(3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl)pyrimidine-2,4(1H,3H)-dione 
• 1350660-75-1 5-(3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl)pyrimidine-2,4(1H,3H)-dione 
• 1350660-73-9 5-(3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl)pyrimidine-2,4(1H, 3H)-dione 
• 1350660-71-7 5-(3-p-tolyl-1,2,4-oxadiazol-5-yl)pyrimidine-2,4(1H,3H)-dione 
• 65906-82-3 5-cyano-6-ethoxy-5-fluoro-5,6-dihydrouracil 
• 66-22-8 uracil 
• 51-21-8 5-fluorouracil 
• 23945-44-0 2,4-dihydroxypyrimidine-5-carboxylic acid 

Relevant academic research and scientific papers

CYCLIZATION DICHOTOMY OF ESTERS OF 3-UREIDO-2-CYANO-2-PROPENOIC AND 3-UREIDO-2-ACYL-2-PROPENOIC ACIDS

The preparation of E and Z isomers of 3-ureido-2-cyano-2-propenoates Ia-Id and their base-catalyzed isomerization and cyclization to 5-carboxycytosine derivatives IIa-IIf and 5-cyanouracil derivatives IIIa and IIIb is described.Also described is the preparation of 3-ureido-2-acyl-2-propenoates Va-Vd and their base-catalyzed cyclization to 5-carboxy-2(1H)-pyrimidone derivatives VIa-VIc and 5-acyluracils VIIa-VIIc.

A microwave-assisted high-efficient synthetic 5-cyanogenetic uracil method

The invention relates to a microwave-assisted high-efficiency method for synthesizing 5-cyanouracil, which comprises the following steps: carrying out microwave radiation on urea, malononitrile and triethyl orthoformate at the microwave reaction temperature of 60-80 DEG C under the microwave power of 500W under atmospheric pressure for 8-20 minutes, and filtering the residual triethyl orthoformate out of the reaction system to obtain a dicyan intermediate I; dissolving the obtained solid in a sodium ethylate 1.0-2.0 mol/L solution, carrying out radiation reaction at the microwave reaction temperature of 30-50 DEG C under the microwave power of 300W under atmospheric pressure for 30-50 minutes, adding activated carbon for decolorization, filtering, and acidifying the filtered precipitate with glacial acetic acid to obtain an intermediate II; and adding 2.5-3.0 mol/L dilute hydrochloric acid into the intermediate II, carrying out radiation at the microwave reaction temperature of 80-100 DEG C under the microwave power of 500W under atmospheric pressure for 30-50 minutes, cooling, and filtering to obtain the 5-cyanouracil.

Pyrimidine derivatives useful as inhibitors of PKC-theta

Disclosed are novel compounds of formula (I): wherein X, Y, R1, R2 and R3 are as defined herein, which are useful as inhibitors of PKC-theta and are thus useful for treating a variety of diseases and disorders that are mediated or sustained through the activity of PKC-theta, including immunological disorders and type II diabetes. This invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.

Uracil reductase inactivators

The present invention relates to a group of 5-substituted uracil derivatives which are inactivators of uracil reductase and which are particularily useful in cancer chemotherapy, especially in combination with antimetabolite antineoplastic agents such as 5-fluorouracil (5-FU).

5-Fluorouracil derivatives

Novel compounds comprising 5-fluorouracil or 5-fluorouridine covalently linked to 5-ethynyluracil, 5-ethynyluridine or 5-propynyluracil and pharmaceutical compositions comprising such compounds are disclosed.

Pharmaceutical compositions of 5-substituted uracil compounds

Pharmaceutical compositions containing 5-substituted uracil compounds are disclosed. The compositions are preferably in the form of a tablet or capsule.

Syntheses with Nitriles, XCV: Deamination of Cytosine Derivatives

Treatment of 2-formyl-3-dimethylamino-propenenitrile (1a) and 2-ethoxycarbonyl-3-dimethylamino-propenenitrile (1b), resp., with substituted ureas led to the 2-cyano-3-ureidoacrylates 2, which can be cyclized under alkaline conditions to give 5-formyl-5-cy