89609-46-1

Usage

Chemical class

Urea derivatives

Composition

Cyclohexyl group and 4-methylphenyl group connected to a urea functional group

Industrial applications

Production of pharmaceuticals, agrochemicals, and dyes

Biological activities

Potential anti-cancer and anti-inflammatory properties

Synthesis utility

Used as a building block in the synthesis of other organic compounds due to unique structural features and reactivity

Diverse uses

Potential applications in various fields

Upstream product

• 108-91-8 cyclohexylamine 
• 622-58-2 p-Tolylisocyanate 
• 106-49-0 p-toluidine 
• 3173-53-3 Cyclohexyl isocyanate 
• 33275-26-2 N-(4-methylphenyl)-O-phenyl carbamate 
• 931-53-3 Cyclohexyl isocyanide 
• 37934-96-6 2,2,2-trichloroethyl N-p-tolylcarbamate 
• 86065-10-3 O-allyl-N-(4-methylphenyl)carbamate 
• 59046-28-5 p-toluoyl-1H-1,2,3-benzotriazole 

Downstream Products

• 89609-48-3 N¹-Cyclohexyl-3--N²-(p-tolyl)propiolamidin 
• 89609-63-2 2-Cyclohexylamino-6-methyl-4-chinolin 
• 89609-45-0 N-cyclohexyl-N'-(p-tolyl)methanediimine 

Relevant academic research and scientific papers

An Improved Synthesis of Urea Derivatives from N -Acylbenzotriazole via Curtius Rearrangement

The good leaving tendency of the benzotriazole moiety has been exploited for the synthesis of symmetric, unsymmetric, N -acyl, and cyclic ureas in good yields from N -acylbenzotriazoles by treating the latter with various amines in the presence of TMSN 3 /Et 3 N in a sealed tube. The salient features of the devised protocol includes the high-yield, mild, metal-free, one-pot reaction conditions, and short reaction time. Furthermore, in many cases, no column chromatography is required for the purification.

CaI2-Catalyzed direct transformation of: N -Alloc-, N -Troc-, and N -Cbz-protected amines to asymmetrical ureas

A novel and facile CaI2-catalyzed direct synthesis of asymmetrical ureas from N-Alloc-, N-Troc-, and N-Cbz-protected amines is developed. In this study, the efficient reaction of Alloc-, Troc-, and Cbz-carbamates with amines in the presence of catalytic CaI2 successfully generated various asymmetrical ureas. This catalytic synthetic procedure provided the desired ureas via reactions of these protected aromatic and aliphatic amines with various amines in high yields without side products. This suggests that novel direct synthesis of ureas from Alloc-, Troc-, and Cbz-carbamates can be a promising approach for the synthesis of useful ureas.

Oximes as reusable templates for the synthesis of ureas and carbamates by an: In situ generation of carbamoyl oximes

Oximes have been identified as reusable templates for the synthesis of ureas and carbamates by an in situ generation of carbamoyl oximes under metal-free conditions. The recovered oxime has been utilised for three trials in the synthesis of urea derivatives without any loss in the yield and efficiency. In addition, this template approach could override the usage of hazardous and less stable isocyanates as substrates.

Cobalt(II)-catalyzed isocyanide insertion reaction with amines under ultrasonic conditions: A divergent synthesis of ureas, thioureas and azaheterocycles

Cobalt(II) acetylacetonate-catalyzed isocyanide insertion reactions with amines utilizing tert-butyl hydroperoxide (TBHP) as an oxidant under ultrasound conditions have been developed, which lead to the synthesis of ureas, thioureas, as well as 2-aminoben

Phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate as carbonyl source: Facile and selective synthesis of carbamates and ureas under mild conditions

The selective syntheses of carbamates, symmetric -ureas, and unsymmetrical ureas have been accomplished by the -reaction of amines with phenyl 4,5-dichloro-6-oxopyridazine-1(6H)-carboxylate as a carbonyl source under mild conditions. It is noteworthy that this process is mild, economic, and convenient.

Structural refinement of inhibitors of urea-based soluble epoxide hydrolases

The soluble epoxide hydrolase (sEH) is involved in the metabolism of arachidonic, linoleic, and other fatty acid epoxides, endogenous chemical mediators that play an important role in blood pressure regulation and inflammation. 1,3-Disubstituted ureas, carbamates, and amides are new potent and stable inhibitors of sEH. However, the poor solubility of the lead compounds limits their use. Inhibitor structure-activity relationships were investigated to better define the structural requirements for inhibition and to identify points in the molecular topography that could accept polar groups without diminishing inhibition potency. Results indicate that lipophilicity is an important factor controlling inhibitor potency. Polar groups could be incorporated into one of the alkyl groups without loss of activity if they were placed at a sufficient distance from the urea function. The resulting compounds had a 2-fold higher water solubility. These findings will facilitate the rational design and optimization of sEH inhibitors with better physical properties.

3-D QSAR analysis of inhibition of murine soluble epoxide hydrolase (MsEH) by benzoylureas, arylureas, and their analogues

Two hundred and seventy-one compounds including benzoylureas, arylureas and related compounds were assayed using recombinant murine soluble epoxide hydrolase (MsEH) produced from a baculovirus expression system. Among all the insect growth regulators assayed, 18 benzoylphenylurea congeners showed weak activity against MsEH. Newly synthesized cyclohexylphenylurea, 1-benzyl-3-phenylurea, and 1,3-dibenzylurea analogues were rather potent. The introduction of a methyl group at the para-position of the phenyl ring of cyclohexylphenylurea enhanced the activity 6-fold, though similar substituent effects were not seen for any of the benzoylphenylureas. The activities of these compounds, including several previously reported compounds, such as dicyclohexylurea, diphenylurea, and their related analogues (Morisseau et al., Proc. Natl. Acad. Sci., 1999, 96, 8849), were quantitatively analyzed using comparative molecular field analysis (CoMFA), a three-dimensional quantitative structure-activity relationship (3-D QSAR) method. Both steric and electrostatic factors contributing to variations in the activity were visualized using CoMFA. CoMFA results showed that one side of the cyclohexylurea moiety having a trans-amide conformation (A-ring moiety) is surrounded by large sterically unfavorable fields, while the other side of A-ring moiety and the other cyclohexyl group (B-ring moiety) is encompassed by sterically favored fields. Electrostatically negative fields were scattered around the entire molecule, and a positive field surrounds the carbon of the carbonyl group. Hydrophobic fields were visualized using Kellogg's hydropathic interaction (HINT) in conjunction with CoMFA. Hydrophobically favorable fields appeared beside the 4- and 4'-carbon atoms of the cyclohexyl groups, and hydrophobically unfavorable fields surrounded the urea bridge. The addition of the molecular hydrophobicity, it> /it>, to CoMFA did not improve the correlation significantly. The ligand-binding interactions shown by X-ray crystallographic data were rationalized using the results of the CoMFA and HINT analyses, and the essential physicochemical parameters for the design of new MsEH inhibitors were disclosed. Copyright (C) 2000 Elsevier Science Ltd.

Secondary amide-based linkers for solid phase organic synthesis

The electron rich benzaldehyde derivatives 4-hydroxybenzaldehyde and 2-methoxy-4-hydroxybenzaldehyde have been investigated for use as linkers for solid phase organic synthesis. Reductive amination of these aldehydes attached to ArgoGel resins with a model primary amine gave the corresponding benzylic secondary amines. These compounds were then converted to the corresponding ureas, sulfonamides, aryl amides, and alkyl amides by derivatization with an appropriate electrophile. The desired secondary amide derivative was then cleaved from the support by treatment with trifluoroacetic acid to provide essentially quantitative yields of products in high purity.