33026-77-6

Usage

Chemical structure

1-(benzyloxy)-3-phenylurea is a chemical compound consisting of a phenylurea group (a carbamate derivative) and a benzyloxy group attached to the nitrogen atom.

Intermediate in synthesis

It is commonly used as an intermediate in the synthesis of pharmaceuticals and organic compounds.

Benzyloxy group

The benzyloxy group is known for its ability to enhance the bioavailability and lipophilicity of the compound, making it suitable for drug development.

Phenylurea group

The phenylurea group imparts stability and reactivity to the molecule, making it a versatile building block for organic synthesis.

Potential applications

The compound has potential applications in the development of drugs for various therapeutic areas such as cancer, inflammation, and infectious diseases.

Bioavailability

The presence of the benzyloxy group enhances the bioavailability of the compound, which is an important factor in drug development.

Lipophilicity

The benzyloxy group also increases the lipophilicity of the compound, which can improve its absorption and distribution in the body.

Stability

The phenylurea group provides stability to the molecule, which is essential for its use in pharmaceuticals and organic synthesis.

Reactivity

The phenylurea group also contributes to the reactivity of the molecule, allowing it to be used as a building block in the synthesis of other compounds.

Therapeutic areas

1-(benzyloxy)-3-phenylurea has potential applications in the development of drugs for various therapeutic areas, including cancer, inflammation, and infectious diseases.

Upstream product

• 622-33-3 N-benzyloxyamine 
• 103-71-9 phenyl isocyanate 
• 62-53-3 aniline 
• 83948-52-1 1-(4-nitrophenol)-N-(O-benzylhydroxy) carbamate 
• 92289-72-0 imidazole-1-carboxylic acid benzyloxyamide 

Downstream Products

• 1007-36-9 1-methyl-3-phenylurea 
• 622-33-3 N-benzyloxyamine 
• 7335-35-5 1-hydroxy-3-phenylurea 
• 53821-11-7 1-hydroxy-1H-benzo[d]imidazol-2(3H)-one 
• 86690-36-0 1-(benzyloxy)-3-methyl-1H-benzo[d]imidazol-2(3H)-one 
• 53821-10-6 1-(benzyloxy)-1,3-dihydro-2H-benzo[d]imidazol-2-one 

Relevant academic research and scientific papers

Vinylogous Aza-Michael Addition of Urea Derivatives with p-Quinone Methides Followed by Oxidative Dearomative Cyclization: Approach to Spiroimidazolidinone Derivatives

Herein, we report an efficient protocol for the synthesis of spiro-imidazolidinone-cyclohexadienones from p-quinone methides (p-QMs) and dialkyloxy ureas under mild conditions. The strategy follows a two-step process involving an initial vinylogous conjugate addition of urea derivatives to p-QMs, followed by oxidative dearomative cyclization of open-chain product to the projected spiro-imidazolidinones. This protocol exhibits good functional group tolerance and provides a straightforward method to access spiro-imidazolidinone-cyclohexadienones. In follow-up chemistry, we have shown the debenzylation of spiroimidazolidinones to give N-hydroxycyclic ureas. (Figure presented.).

[3+3] Annulation via Ring Opening/Cyclization of Donor–Acceptor Cyclopropanes with (Un)symmetrical Ureas: A Quick Access to Highly Functionalized Tetrahydropyrimidinones

A mild and straight-forward access to pharmacologically privileged tetrahydropyrimidinones exploiting readily available Donor–Acceptor cyclopropanes (DACs) is reported. This methodology involves the Lewis acid catalyzed synthesis of uriedo-malonates from (un)symmetrical ureas and DACs followed by I2-base mediated cyclization to their corresponding tetrahydropyrimidinones. The cyclization protocol involves nucleophilic attack of the nitrogen of urea on the newly generated electrophilic acceptor end of DAC. The post functionalization offered potential biologically active molecules.

Synthesis and SAR of 1-hydroxy-1 H -benzo[ d ]imidazol-2(3 H)-ones as inhibitors of d -amino acid oxidase

A series of 1-hydroxy-1H-benzo[d]imidazol-2(3H)-ones were synthesized and evaluated for their ability to inhibit human and porcine forms of d-amino acid oxidase (DAAO). The inhibitory potency is largely dependent on the size and position of substituents o

A convenient method for the synthesis of N-hydroxyureas

Treatment of amines with 1-(4-nitrophenol)-N-(O-benzylhydroxy)carbamate yields the O-benzyl protected N-hydroxyureas. Hydrogenation of the O-benzyl protected N-hydroxyureas over 5% Pd/BaSO4 cleanly gives the N-hydroxyureas in good yield. In add

N-substituted hydroxyureas as urease inhibitors

In order to seek a urease inhibitor more potent than hydroxyurea (1), its alkyl- or phenyl-substituted derivatives were synthesized and evaluated for their effect on the jack bean urease. Of 16 compounds tested, m-methyl-(10) and m-methoxy-phenyl substituted hydroxyurea (13) showed the most potent inhibitory activities against the enzyme.

Synthesis of 3-hydroxypyrimidine-2,4-diones. Addition of anilines to benzyloxy isocyanate synthons to give N-hydroxyureas

A new method, the addition of N-benzyloxychloroformate to methyl anthranilate followed by base-catalyzed cyclization, has been employed to synthesize the N-hydroxyquinazolinedione 1 and heterocyclic derivatives. N-Benzyloxycarbonylimidazole is a useful sy

Reactions of N-Acyl-O-alkylhydroxylamines and Alkoxyamines with Isocyanates and Isothiocyanates

A number of N-acyl-O-alkylhydroxylamines(II) have been prepared by alkylation of potassium salts of hydroxamic acids under weakly basic conditions.Acid hydrolysis of N-acyl-O-alkylhydroxylamines(II) followed by treatment with base affords alkoxyamines in good yield.The reactions of N-acyl-O-alkylhydroxylamines and alkoxyamines with phenyl isocyanate, p-nitrophenyl isocyanate, α-naphthyl isocyanate and phenyl isothiocyanate have been studied and the products obtained characterized by spectral (IR, NMR) data.