20295-24-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Ethyl-6-Chlorouracil is used as a building block for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Ethyl-6-Chlorouracil is utilized as a precursor in the synthesis of agrochemicals, contributing to the development of new products with potential applications in agriculture.
Used in Antitumor Research:
5-Ethyl-6-Chlorouracil is studied for its potential antitumor properties, making it a candidate for further research and development as a therapeutic agent against cancer.
Used in Antiviral Research:
5-ETHYL-6-CHLOROURACIL is also being investigated for its potential antiviral properties, indicating its possible use in the development of treatments for viral infections.
Used in Research and Studies:
5-Ethyl-6-Chlorouracil is used in research and studies related to uracil derivatives and their biological activities, contributing to the understanding of the structure-activity relationships in this class of compounds and potentially leading to the discovery of new therapeutic agents.

InChI:InChI=1/C6H7ClN2O2/c1-2-3-4(7)8-6(11)9-5(3)10/h2H2,1H3,(H2,8,9,10,11)

Upstream product

• 2518-72-1 5-ethyl barbituric acid 
• 120268-44-2 5-ethyl-6-chloro-2,4-dimethoxypyrimidine 
• 133-13-1 ethyl diethyl malonate 
• 1780-38-7 2,4,6-trichloro-5-ethylpyrimidine 

Downstream Products

• 172256-32-5 1-Benzyloxymethyl-6-chloro-5-ethyl-1H-pyrimidine-2,4-dione 
• 1310053-25-8 6-[4-(2-methoxyphenyl)-1-piperazinyl]-5-ethyluracil 
• 1310053-24-7 6-(4-phenyl-1-piperazinyl)-5-ethyluracil 
• 172256-05-2 1-[(benzyloxy)methyl]-6-[(3,5-dimethylphenyl)selenenyl]-5-ethyluracil 
• 172256-02-9 6-(3,5-Dimethyl-phenylselanyl)-1-ethoxymethyl-5-ethyl-1H-pyrimidine-2,4-dione 
• 155831-53-1 1-<(benzyloxy)methyl>-5-ethyl-6-(phenylselenenyl)uracil 
• 867038-75-3 1-[(benzyloxy)methyl]-5-ethyl-6-(1-nitro-2-naphthylthio)uracil 
• 867038-78-6 1-[(benzyloxy)methyl]-5-ethyl-6-(1-amino-2-naphthylthio)uracil 
• 152433-65-3 6-phenylthio-5-ethyuracil 
• 171048-61-6 5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 
• 100763-60-8 6-Benzylamino-5-ethyl-1H-pyrimidine-2,4-dione 
• 100763-64-2 5-Ethyl-6-p-tolylamino-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Synthesis and antimicrobial activity of some novel 5-alkyl-6-substituted uracils and related derivatives

6-Chloro-5-ethyl-, n-propyl- and isopropyluracils 5a-c were efficiently prepared from the corresponding 5-alkybarbituric acids 3a-c via treatment with phosphorus oxychloride and N,N-dimethylaniline to yield the corresponding 5-alkyl-2,4,6-trichloropyrimidines 4a-c, which were selectively hydrolyzed by heating in 10% aqueous sodium hydroxide for 30 minutes. The reaction of compounds 5a-c with 1-substituted piperazines yielded the corresponding 5-alkyl-6-(4-substituted-1-piperazinyl)uracils 6a-j. The target 8-alkyltetrazolo[1,5-f]pyrimidine-5,7(3H,6H)-diones 7a-c were prepared via the reaction of 5a-c with sodium azide. Compounds 6a-j and 7a-c were tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compound 6h displayed potent broad-spectrum antibacterial activity, while compound 6b showed moderate activity against the Gram-positive bacteria. All the tested compounds were practically inactive against Candida albicans.

Discovery of 5-substituted-6-chlorouracils as efficient inhibitors of human thymidine phosphorylase

Thymidine phosphorylase plays an important role in angiogenesis, which is an attractive target for therapy of cancer and other diseases. In our continuous effort to develop novel inhibitors of thymidine phosphorylase, we have discovered that 6-halouracils substituted at position C5 by certain hydrophobic groups exhibit significant inhibitory activity against this enzyme. The most potent compounds bear a five- or six-membered cyclic substituent containing a π-electron system at C5 and a chlorine atom attached at C6. 6-Chloro-5-cyclopent-1-en-1-yluracil 7a is the most efficient derivative in this study, with Ki = 0.20 ± 0.03 μM (Ki/ dThdKm = 0.0017) for thymidine phosphorylase expressed in V79 cells and Ki = 0.29 ± 0.04 μM (Ki/ dThdKm = 0.0024) for the enzyme purified from placenta.

Synthesis of certain 6-(arylthio)uracils as potential antiviral agents

A series of 6-(Arylthio)uracils have been prepared via condensation of 6-chlorouracil or 5-ethyl-6-chlorouracil with the corresponding thiopnenol derivatives in pyridine or ethanolic potassium hydroxide. The synthesized compounds were tested for their antiviral activity. Some of the 5-ethyl-6-(arylthio)uracil derivatives 10a-g showed moderate activities against hepatitis B Virus (HBV) and HIV-1 virus.

Antiviral 2, 4-pyrimidinedione derivatives

Novel 2,4-pyrimidinedione compounds, and pharmaceutically acceptable salts thereof which possess good antiviral activities, and specifically represented by the following formula(I): STR1 wherein: R 1 represents an unsubstituted or substituted allyl group represented by CH 2 CH CR 5 R 6 or an unsubstituted or substituted propargyl group represented by CH 2 C CR 7 wherein R 5, R 6 and R 7 are each independently a hydrogen atom; a methyl group optionally substituted with a halogen atom, or a C 1-10 carbonyloxy, hydroxy, azido, cyano, optionally substituted amino, optionally substituted phosphonyl, optionally substituted phenyl, C 3-10 heteroaryl, C 1-3 alkoxy or benzyloxy radical; a C 2-10 alkyl or alkenyl group; a cyclopropyl group; an optionally substituted phenyl group; a C 3-10 heteroaryl group; a C 1-10 ester group; or an optionally substituted C 1-10 alkylamide group;R 2 represents a halogen atom, an optionally substituted C 1-5 alkyl, C 3-6 cycloalkyl, C 2-8 alkenyl, C 2-8 alkynyl group or a benzyl group;R 3 and R 4 represent independently a hydrogen or halogen atom, or a hydroxy, C 1-3 alkyl, fluoromethyl, C 1-3 alkoxy, amino, C 2-6 alkylester or C 2-7 alkylamide group;A represents an oxygen or sulfur atom;Z represents an oxygen or sulfur atom; a carbonyl group; an amino group; or a methylene group optionally substituted with at least one selected from the group consisting of a halogen atom, and a cyano, hydroxy, azido, amino, C 1-3 alkylamide, C 1-4 ester, and nitro groups.

A New Route to the Improved Synthesis of 1-(Alkoxymethyl)-5-alkyl- 6-(arylselenenyl)uracils

A new route to C-6-selenenyl analogs of compound 1a from 5-alkyl-6-chlorouracils 6a-b has been described. A mild and highly efficient synthesis of 1-(alkoxymethyl)-5-alkyl-6-(arylselenenyl)uracils 8a-e has been accomplished from 6a-b in good yields using a two step procedure. Silylation of 5-alkyl-6-chlorouracils 6a-b using N,O-bis(trimethylsilyl)acetamide followed by regioselective alkylation of the silylated intermediate with ethyl or benzyl chloromethyl ether in dichloromethane afforded the desired 1-(alkoxymethyl)-5-alkyl-6-chlorouracils 7a-d in 88-94% yields. Compounds 7a-d readily underwent addition-elimination reaction with an appropriate arylselenol in the presence of ethanolic sodium hyroxide to produce the corresponding 1-(alkoxymethyl)-5-alkyl-6-(arylselenenyl)uracils 8a-e in excellent yields (94-99%).