191472-79-4

Basic information

• Product Name: 5-Cyclopropyl-6-methanesulfonyl-1-phenethyloxy-1H-pyrimidine-2,4-dione
• Synonyms: 5-Cyclopropyl-6-methanesulfonyl-1-phenethyloxy-1H-pyrimidine-2,4-dione
• CAS NO: 191472-79-4
• Molecular Weight: 350.395
• Mol File: 191472-79-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-Cyclopropyl-6-methanesulfonyl-1-phenethyloxy-1H-pyrimidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Cyclopropyl-6-methanesulfonyl-1-phenethyloxy-1H-pyrimidine-2,4-dione(191472-79-4)
• EPA Substance Registry System: 5-Cyclopropyl-6-methanesulfonyl-1-phenethyloxy-1H-pyrimidine-2,4-dione(191472-79-4)

Safety Data

• Hazardous Substances Data: 191472-79-4(Hazardous Substances Data)

Upstream product

• 191472-53-4 5-Cyclopropyl-6-methylsulfanyl-1-phenethyloxy-1H-pyrimidine-2,4-dione 
• 92856-14-9 2-phenethoxyisoindoline-1,3-dione 
• 4732-11-0 O-(2-phenylethyl)hydroxylamine 
• 60-12-8 2-phenylethanol 
• 191473-30-0 2-cyclopropyl-3,3-bis(methylthio)acrylic acid 
• 191473-33-3 2-cyclopropyl-3,3-bis(methylthio)acryloyl chloride 
• 191473-28-6 ethyl 2-cyclopropyl-3,3-bis(methylthio)acrylate 
• 1026928-27-7 2-Cyclopropyl-3,3-bis-methylsulfanyl-acryloyl isocyanate 
• 191472-26-1 C₁₇H₂₂N₂O₃S₂ 

Relevant articles and documents

Synthesis and anti-HIV-1 activity of a series of 1-alkoxy-5-alkyl-6- (arylthio)uracils

A series of 1-alkoxy-5-alkyl-6-(arylthio)uracils was synthesized and tested for their ability to inhibit HIV-1 replication. Treatment of 2-alkyl- 3,3-bis(methylthio)acryloyl chlorides (5a-e) with AgOCN in benzene followed by reaction of the resulting isocyanates 6a-e with an appropriate alkoxyamine gave N-alkoxy-N'-((2-alkyl-3,3-bis(methylthio)acryloyl)ureas (10a-z) in good to excellent yields. Cyclization of 10a-z in AcOH containing a catalytic amount of p-TsOH produced 1-alkoxy-5-alkyl-6-(methylthio)uracils (11a-z). Oxidation of 11a-z with 3-chloroperoxybenzoic acid in CH2Cl2 resulted in high yields of 1-alkoxy-5-alkyl-6-(methylsulfonyl)uracils (12a-x and 12z) and 1-(benzyloxy)-6-(methylsulfinyl)thymine (12y), which were subsequently reacted with an appropriate arenethiol in ethanolic NaOH solution to afford 1-alkoxy-5-alkyl-6-(arylthio)uracils (14-49). Substitution at the 3- and 5- positions of the C-6-(phenylthio) ring by two methyl groups significantly increased its original anti-HIV-1 activity (EC50: 6-((3,5- dimethylphenyl)thio)-5-isopropyl-1-propoxyuracil (18), 0.064 μM; 6-((3,5- dimethylphenyl)thio)-1-(3-hydroxypropoxy)-5-isopropyluracil (23), 0.19 μM). Among the various alkoxy substituents at the N-1, the propoxy group was the most beneficial for improving the anti-HIV-1 activity. The 1-propoxy derivative 18 proved to be the most potent inhibitor of HIV-1 replication, followed by the 1-(3-hydroxypropoxy) derivative 23. Introduction of an isopropyl group at C-5 of the uracil base also remarkably enhanced the activity. When compound 18 was incubated with a rat liver homogenate preparation, no metabolite was observed, thus confirming the metabolic stability of the N-O bond in these 1-alkoxyuracils.