75461-45-9

Upstream product

• 100-28-7 4-Nitrophenyl isocyanate 
• 108-91-8 cyclohexylamine 
• 3173-53-3 Cyclohexyl isocyanate 
• 100-01-6 4-nitro-aniline 
• 636-98-6 p-nitrobenzene iodide 
• 67-66-3 chloroform 
• 2733-41-7 4-nitrobenzoyl azide 

Downstream Products

• 62972-70-7 1-(4-aminophenyl)-3-cyclohexylurea 

Relevant academic research and scientific papers

Discovery of novel 2,4-disubstituted pyrimidines as Aurora kinase inhibitors

In order to explore novel Aurora kinase inhibitors, a series of novel 2,4-disubstituted pyrimidines were designed, synthesized and evaluated their in vitro anti-proliferative activities against a panel of cancerous cell lines (A549, HCT-116 and MCF-7). Among them, compound 12a showed the moderate to high anti-proliferative activities against A549 (IC50 = 12.05 ± 0.45 μM), HCT-116 (IC50 = 1.31 ± 0.41 μM) and MCF-7 (IC50 = 20.53 ± 6.13 μM) cells, as well as the Aurora A and Aurora B inhibitory activities with the IC50 values of 309 nM and 293 nM, respectively. Furthermore, compound 12a induced apoptosis by upregulated the pro-apoptotic proteins Bax and decreased the anti-apoptotic protein Bcl-xl in HCT-116 cells. Moreover, the molecular docking study showed that compound 12a had good binding modes with Aurora A and Aurora B and the bioinformatics prediction discovered that compound 12a exhibited good drug likeness using SwissADME. Taken together, these results indicated that 12a may be a potential anticancer compound that was worthy of further development as Aurora kinase inhibitor.

Synthesis of Novel 3-N-substituted Carbazole Derivatives and Evaluation of their Abilities to Inhibit Platelet Aggregation

The carbazole moiety exhibits various biological activities, including anticancer, antiviral, anti-inflammatory, and antimicrobial activities; some compounds containing the moiety also inhibit platelet aggregation. In the present study, we synthesized a series of 3-N-substituted carbazole derivatives and evaluated their abilities to inhibit in vitro platelet aggregation induced by collagen (5 μg/mL). Of the synthesized compounds, compound 5q (JSCa15), with a urea linkage within the carbazole framework, exhibited the strongest inhibitory activity (98.25% at 30 μM). Interestingly, reduction of the nitro group of compound 5q to an amine exhibited significantly decreased activity (compound 5r, 5.18% at 30 μM). Also, substitution of the urea moiety of compound 5q with a carbamate moiety resulted in a considerable loss of activity (compound 8a, 5.91% at 30 μM). These results suggest that the urea moieties and nitro groups of 3-N-substituted carbazole derivatives may play key roles in inhibiting in vitro platelet aggregation induced by collagen.

Pd/C-Catalyzed Domino Synthesis of Urea Derivatives Using Chloroform as the Carbon Monoxide Source in Water

A Pd/C-catalyzed domino synthesis of symmetrical and unsymmetrical ureas from aryl iodides, sodium azide, amines and CHCl3 in water has been developed. This reaction proceeds with sequential carbonylation, Curtius rearrangement and nucleophilic addition. CHCl3 serves as a convenient and safe alternation of CO gas in the presence of KOH. A series of urea derivatives were obtained in moderate to good yields with good functional group tolerance. Furthermore, the Pd/C catalyst could be readily recovered with slight decrease in the catalytic activity after six consecutive runs. (Figure presented.).

A new class of low-molecular-weight amphiphilic gelators

A new powerful class of low-molecular-weight amphiphilic compounds has been synthesized and their structure-property relationships with respect to their gelation ability of organic solvents have been investigated. These compounds are able to gel organic solvents over a broad range of polarity. Especially polar solvents such as valeronitrile and γ-butyrolactone can be gelled even at concentrations far below 1 wt %. It was found that the gelation ability of these asymmetrically substituted p-phenylendiamines depends on a well-balanced relation of the terminal head group, the units involved in hydrogen bonding (amide or urea groups), and on the length of the alkyl chain. With this class of new gelators it is possible to tailor thermal and mechanical properties in different organic solvents and open various application possibilities.

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.