155831-53-1

Basic information

• Product Name: 1-[(benzyloxy)methyl]-5-ethyl-6-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione
• CAS NO: 155831-53-1
• Molecular Formula: C₂₀H₂₀N₂O₃Se
• Molecular Weight: 415.3444
• Mol File: 155831-53-1.mol

Chemical Properties

• CAS DataBase Reference: 1-[(benzyloxy)methyl]-5-ethyl-6-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(benzyloxy)methyl]-5-ethyl-6-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione(155831-53-1)
• EPA Substance Registry System: 1-[(benzyloxy)methyl]-5-ethyl-6-(phenylselanyl)pyrimidine-2,4(1H,3H)-dione(155831-53-1)

Safety Data

• Hazardous Substances Data: 155831-53-1(Hazardous Substances Data)

Usage

Chemical class

Pyrimidine derivatives

Heterocyclic compound

Yes

Composition

Pyrimidine ring with additional functional groups

Functional groups

Ethyl group, phenylselanyl group, benzyloxymethyl group

Presence of heteroatoms

Carbon, Hydrogen, Nitrogen, Oxygen, Selenium

Potential applications

Pharmaceuticals, agrochemicals, materials science

Structure significance

Unique properties due to functional groups

Research and development

Interesting target for further exploration

Molecular weight

Approximately 403.35 g/mol

Appearance

Likely a solid or crystalline compound (based on typical properties of similar compounds)

Solubility

Solvent compatibility not provided, but likely soluble in organic solvents (e.g., methanol, ethanol, acetone) due to the presence of the ethyl and phenyl groups

Stability

Stability information not provided, but generally stable under normal conditions for organic compounds

Reactivity

Reactivity information not provided, but may be influenced by the presence of the phenylselanyl group and the pyrimidine ring

Synthesis

Synthesis method not provided, but likely involves the formation of the pyrimidine ring and subsequent functionalization with the ethyl, phenylselanyl, and benzyloxymethyl groups

Upstream product

• 1666-13-3 diphenyl diselenide 
• 153562-61-9 5-ethyl-1-(benzyloxymethyl)uracil 
• 645-96-5 Benzeneselenol 
• 172256-32-5 1-Benzyloxymethyl-6-chloro-5-ethyl-1H-pyrimidine-2,4-dione 
• 2518-72-1 5-ethyl barbituric acid 
• 20295-24-3 5-ethyl-6-chloro-2,4-pyrimidinedione 

Relevant articles and documents

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%).

Synthesis and anti-HIV-1 activities of 6-arylthio and 6- arylselenoacyclonucleosides

6-Arylthio and 6-arylselenoacyclonucleosides was synthesized and tested for the ability to inhibit replication of HIV-1. Lithiation of acyclonucleosides with LDA followed by reaction with the electrophiles phenyl disulfide, diphenyl diselenide, 2,2'-dipyrdyl disulfide or 2,2'-dipyridyl diselenide afforded 6-(arylthio or arylseleno)acyclonucleosides 5a-c, 6, 7, 9, 15a-c, 17a-c. Compounds 19a-c and 20a-c were obtained by deprotection of corresponding TBDMS derivatives. Dehydrated products 16a, and 18a-c were also formed during the reactions. 5-Ethyl-6-(α-pyridylthio or α-pyridylseleno) disubstituted acyclouracils 6 and 7 were more active against HIV-1 in both MT-2 and CEM-IW cell lines than AZT, DDC, DDI or D4T. The EC50 of 6 against HIV-1 in CEM-IW cell was in the nanomolar range with a therapeutic index of 1100.