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Usage

Uses

Used in Pharmaceutical Industry:
5-Benzyloxybenzylacyclouridine is used as a pharmaceutical compound for its potential therapeutic properties. Its unique structure may allow it to interact with specific biological targets, such as enzymes or receptors, and modulate their activity. This could lead to the development of new drugs for the treatment of various diseases.
Used in Drug Delivery Systems:
In the field of drug delivery, 5-benzyloxybenzylacyclouridine can be employed as a carrier or component of a drug delivery system. Its chemical properties may enable it to encapsulate or conjugate with therapeutic agents, improving their stability, solubility, and targeted delivery to specific tissues or cells.
Used in Chemical Research:
5-Benzyloxybenzylacyclouridine can also be utilized in chemical research as a model compound for studying the synthesis, properties, and reactivity of benzyl ether derivatives. This may contribute to the development of new synthetic methods, as well as a better understanding of the structure-activity relationships in this class of compounds.
Used in Material Science:
The unique structure of 5-benzyloxybenzylacyclouridine may also find applications in material science, where it could be used to develop new materials with specific properties. For example, it could be incorporated into polymers or other materials to impart desired characteristics, such as improved stability, solubility, or biocompatibility.

InChI:InChI=1/C21H22N2O5/c24-9-10-27-15-23-13-18(20(25)22-21(23)26)11-17-7-4-8-19(12-17)28-14-16-5-2-1-3-6-16/h1-8,12-13,24H,9-11,14-15H2,(H,22,25,26)

Upstream product

• 100-39-0 benzyl bromide 
• 28495-92-3 5-(3-benzyloxy-benzyl)-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 28495-80-9 5-(m-(benzyloxy)benzyl)acyclouridine 
• 75849-10-4 ethyl 3-<3-(benzyloxy)phenyl>propanoate 
• 34708-60-6 3-(3-hydroxy-phenyl)propionic acid ethyl ester 

Downstream Products

• 110522-16-2 5-benzyloxybenzyl-1-<(2-(3-carboxypropionyloxy)ethoxy)methyl>uracil 
• 105847-69-6 5-(3-hydroxybenzyl)-1-<(2-hydroxyethoxy)methyl>uracil 

Relevant academic research and scientific papers

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.