82857-69-0

Basic information

• Product Name: 5-benzylacyclouridine
• Synonyms: 5-benzylacyclouridine;5-Benzyl-1-(2-hydroxyethoxymethyl)uracil
• CAS NO: 82857-69-0
• Molecular Formula: C₁₄H₁₆N₂O₄
• Molecular Weight: 276.2878
• Mol File: 82857-69-0.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.29g/cm³
• Refractive Index: 1.583
• CAS DataBase Reference: 5-benzylacyclouridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-benzylacyclouridine(82857-69-0)
• EPA Substance Registry System: 5-benzylacyclouridine(82857-69-0)

Safety Data

• Hazardous Substances Data: 82857-69-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
5-Benzylacyclouridine is used as a research compound for studying its potential therapeutic effects and mechanisms of action. Its unique structure allows it to interact with biological targets, making it a candidate for the development of new drugs.
Used in Chemical Synthesis:
In the chemical industry, 5-benzylacyclouridine can be used as a building block or intermediate in the synthesis of more complex organic molecules. Its benzyl and 2-hydroxyethoxymethyl substituents provide opportunities for further functionalization and modification, expanding its utility in organic chemistry.
Used in Drug Development:
5-Benzylacyclouridine is used as a lead compound in drug discovery, where its properties and interactions with biological systems are investigated. This can lead to the identification of new drug candidates with improved efficacy, safety, and pharmacokinetic profiles.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-benzylacyclouridine serves as a valuable tool for understanding the structure-activity relationships of uracil-based compounds. This knowledge can be applied to optimize the design of new therapeutic agents targeting specific diseases or conditions.
Used in Biochemical Studies:
5-Benzylacyclouridine can be employed in biochemical research to probe the interactions between nucleic acid bases and their binding partners. This can provide insights into the molecular mechanisms underlying various biological processes and contribute to the development of targeted therapies.

InChI:InChI=1/C14H16N2O4/c17-6-7-20-10-16-9-12(13(18)15-14(16)19)8-11-4-2-1-3-5-11/h1-5,9,17H,6-8,10H2,(H,15,18,19)

Upstream product

• 118380-80-6 5-benzyl-1-(2-acetoxyethoxymethyl)uracil 
• 18493-83-9 5-benzyluracil 
• 25912-36-1 5-benzyl-2-tioxo-2,3-dihydro-pyrimidine-4(1H)-one 
• 2021-28-5 ethyl dihydrocinnamate 
• 96328-46-0 5-benzyl-2,4-bis(trimethylsilyloxy)pyrimidine 

Downstream Products

• 110522-15-1 5-benzyl-1-<(2-(3-carboxypropionyloxy)ethoxy)methyl>uracil 
• 110522-22-0 5-benzyl-3-N-(4-benzyloxybenzyl)-1-<(2-hydroxyethoxy)methyl>uracil 

Relevant articles and documents

Inhibition of uridine phosphorylase. Synthesis and structure-Activity relationships of aryl-substituted 1-((2-hydroxyethoxy)methyl)-5-(3- phenoxybenzyl)uracil

Structure-activity relationship studies on a series of 1-((2- hydroxyethoxy)methyl)-5-(3-(substituted-phenoxy)benzyl)uracils as inhibitors of murine liver uridine phosphorylase have led to compounds with IC50s as low as 1.4 nM. The two most potent compounds, 10j (3-cyanophenoxy) and 11f (3-chlorophenoxy) were tested in vive for effects on steady-state concentrations of circulating uridine in mice and rats. Both compounds were substantially more efficacious than BAU (5-benzylacyclouridine) both in vitro and in vivo.

Inhibition of uridine phosphorylase: Synthesis and structure-activity relationships of aryl-substituted 5-benzyluracils and 1-[(2- hydroxyethoxy)methyl]-5-benzyluracils

A series of 1-[(2-hydroxyethoxy)methyl]-5-benzyluracils were synthesized and tested for inhibition of murine liver uridine phosphorylase (UrdPase). Inhibitors of UrdPase are reported to enhance the chemotherapeutic utility of 5-fluoro-2'-deoxyuridine and 5-fluorouracil and to ameliorate zidovudine- induced anemia in animal models. We prepared a series of 5-aryl-substituted analogues of 5-benzylacyclouridine (BAU), a good inhibitor of UrdPase (IC50 of 0.46 μM), to develop a compound with enhanced potency and improved pharmacokinetics. The first phase of structure-activity relationship studies on a series of 32 aryl-substituted 5-benzyluracils found several 5-(3- alkoxybenzyl) analogues of 5-benzyluracil with enhanced potency. The acyclovir side chain, the (2-hydroxyethoxy)methyl group, was substituted on the more potent aryl-substituted 5-benzyluracils. The two most potent compounds, 10y (3-propoxy) and 10dd (3-sec-butoxy), were inhibitors of UrdPase with IC50s of 0.047 and 0.027 μM, respectively. Six compounds were tested in vivo for effects on steady-state concentrations of circulating uridine in rats. Plasma uridine levels were elevated 3-9-fold by compound levels that ranged from 8 to 50 μM.

A NEW METHOD FOR THE SYNTHESIS OF 5-BENZYL-1-(2-HYDROXYETHOXY METHYL)URACIL (BAU), A POTENT URIDINE PHOSPHORYLASE INHIBITOR, AND ITS N3-AND N1,N3-SUBSTITUTED ANALOGS

A new mmethodology for the synthesis of 5-benzyl-1-(2-hydroxyethoxy methyl)uracil (BAU) (1), a potent uridine phosphorylase inhibitor, has been developed.The couping of bis(trimethylsilyl) derivative of 5-brnzyl uracil with 2-acetoxyethoxymethyl bromide,