172256-31-4

Basic information

• Product Name: 1-[(benzyloxy)methyl]-6-chloro-5-isopropyluracil
• Synonyms: 1-[(benzyloxy)methyl]-6-chloro-5-isopropyluracil
• CAS NO: 172256-31-4
• Molecular Weight: 308.765
• Mol File: 172256-31-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-[(benzyloxy)methyl]-6-chloro-5-isopropyluracil(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(benzyloxy)methyl]-6-chloro-5-isopropyluracil(172256-31-4)
• EPA Substance Registry System: 1-[(benzyloxy)methyl]-6-chloro-5-isopropyluracil(172256-31-4)

Safety Data

• Hazardous Substances Data: 172256-31-4(Hazardous Substances Data)

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 96796-80-4 5-isopropyl-6-chloro-2,4-pyrimidinedione 
• 7391-69-7 5-isopropylbarbituric acid 

Downstream Products

• 172256-10-9 1-[(benzyloxy)methyl]-5-isopropyl-6-(phenylselenenyl)uracil 

Relevant articles and documents

Nonnucleoside HIV-1 reverse-transcriptase inhibitors, part 5.1) synthesis and anti-HIV-1 activity of novel 6-naphthylthio HEPT analogues

As part of a series of studies to discover new HIV reverse-transcriptase inhibitors, various novel 6 α- and 6 β-naphthylthio 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio) thymine (HEPT) derivatives were synthesized, and in vitro anti-HIV-1 activity was evaluated. The results revealed that most of 6α-naphthylthio HEPT derivatives (7a - w) showed good activity [for 7e, IC50 value of 0.048 μM and selectivity index (SI) value of 735; for 7h, IC50 value of 0.057 μM and SI value of 579; for 7k, IC50 value of 0.063 μM and SI value of 565], 6 β-naphthylthio HEPT derivatives (8a - f) showed low activity, but the introduction of α nitro group to the C-1 position of the 6 β-naphthyl ring in the 6 β-naphthylthio series (11a - c) resulted in a dramatic increase in anti-HIV-1 activity.

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%).