13252-25-0

Basic information

• Product Name: Urea, N-(4-chlorophenyl)-N'-(4-nitrophenyl)-
• Synonyms: N-(4-Chlor-phenyl)-N'-(4-nitro-phenyl)-harnstoff;N-(p-Chlorphenyl)-N'-(p-nitrophenyl)-harnstoff;1-(4-chlorophenyl)-3-(4-nitrophenyl)urea;4-chlorophenyl(4-nitrophenyl)urea;N-(4-chloro-phenyl)-N'-(4-nitro-phenyl)-urea;N'-p-Nitrophenyl-N-p-chlorphenylharnstoff;1-(4-Chloro-phenyl)-3-(4-nitro-phenyl)-urea
• CAS NO: 13252-25-0
• Molecular Formula: C13H10ClN3O3
• Molecular Weight: 291.694
• Mol File: 13252-25-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 250 °C
• CAS DataBase Reference: Urea, N-(4-chlorophenyl)-N'-(4-nitrophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Urea, N-(4-chlorophenyl)-N'-(4-nitrophenyl)-(13252-25-0)
• EPA Substance Registry System: Urea, N-(4-chlorophenyl)-N'-(4-nitrophenyl)-(13252-25-0)

Safety Data

• Hazardous Substances Data: 13252-25-0(Hazardous Substances Data)

Upstream product

• 100-28-7 4-Nitrophenyl isocyanate 
• 106-47-8 4-chloro-aniline 
• 104-12-1 p-chlorphenylisocyanate 
• 100-01-6 4-nitro-aniline 
• 636-97-5 N-amino-(4-nitrophenyl)carboxamide 
• 619-50-1 4-nitrobenzoic acid methyl ester 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 1073974-15-8 S-p-nitrophenyl N-p-chlorophenylthiocarbamate 
• 2733-41-7 4-nitrobenzoyl azide 
• 99137-12-9 4-Chloro-N-(4-nitro-phenyl)-benzimidoyl chloride 
• 39193-07-2 N-(4-nitrophenyl)-4-chlorophenyl carboxamide 
• 99137-14-1 5-(4-chlorophenyl)-1-(4-nitrophenyl)tetrazole 
• 21368-28-5 4-chlorobenzoyl azide 

Downstream Products

• 50906-33-7 1-(4-aminophenyl)-3-(4-chlorophenyl)urea 

Relevant articles and documents

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.

Discovery of N-phenyl-(2,4-dihydroxypyrimidine-5-sulfonamido) phenylurea-based thymidylate synthase (TS) inhibitor as a novel multi-effects antitumor drugs with minimal toxicity

Thymidylate synthase (TS) is a hot target for tumor chemotherapy, and its inhibitors are an essential direction for anti-tumor drug research. To our knowledge, currently, there are no reported thymidylate synthase inhibitors that could inhibit cancer cell migration. Therefore, for optimal therapeutic purposes, combines our previous reports and findings, we hope to obtain a multi-effects inhibitor. This study according to the principle of flattening we designed and synthesized 18 of N-phenyl-(2,4-dihydroxypyrimidine-5-sulfonamido)phenyl urea derivatives as multi-effects inhibitors. The biological evaluation results showed that target compounds could significantly inhibit the hTS enzyme, BRaf kinase and EGFR kinase activity in vitro, and most of the compounds had excellent anti-cell viability for six cancer cell lines. Notably, the candidate compound L14e (IC50 = 0.67 μM) had the superior anti-cell viability and safety to A549 and H460 cells compared with pemetrexed. Further studies had shown that L14e could cause G1/S phase arrest then induce intrinsic apoptosis. Transwell, western blot, and tube formation results proved that L14e could inhibit the activation of the EGFR signaling pathway, then ultimately achieve the purpose of inhibiting cancer cell migration and angiogenesis in cancer tissues. Furthermore, in vivo pharmacology evaluations of L14e showed significant antitumor activity in A549 cells xenografts with minimal toxicity. All of these results demonstrated that the L14e has the potential for drug discovery as a multi-effects inhibitor and provides a new reference for clinical treatment of non-small cell lung cancer.

Design and discovery of 4-anilinoquinazoline-urea derivatives as dual TK inhibitors of EGFR and VEGFR-2

EGFR and VEGFR-2 are involved in pathological disorders and the progression of different kinds of tumors, the combined blockade of EGFR and VEGFR signaling pathways appears to be an attractive approach to cancer therapy. In this work, a series of 4-anilinoquinazoline derivatives containing substituted diaryl urea or glycine methyl ester moiety were designed and identified as EGFR and VEGFR-2 dual inhibitors. Compounds 19i, 19j and 19l exhibited the most potent inhibitory activities against EGFR (IC50?=?1?nM, 78?nM and 51?nM, respectively) and VEGFR-2 (IC50?=?79?nM, 14?nM and 14?nM, respectively), they showed good antiproliferative activities as well. Molecular docking established the interaction of 19i with the DFG-out conformation of VEGFR-2, suggesting that they might be type II kinase inhibitors.