2000-54-6

Usage

Uses

Used in Pharmaceutical Industry:
N-(3-Nitrophenyl)-N''-phenylurea is used as an intermediate in the synthesis of various pharmaceuticals for its potential biological activity, including anti-tumor and anti-inflammatory properties. Its unique structure allows for the development of new drugs with targeted therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical industry, N-(3-Nitrophenyl)-N''-phenylurea serves as an intermediate in the production of various agrochemicals, such as pesticides and herbicides. Its chemical properties enable the creation of effective compounds for crop protection and management.
Used in Organic Synthesis:
N-(3-Nitrophenyl)-N''-phenylurea is utilized as a versatile intermediate in organic synthesis, allowing for the development of a wide range of organic compounds with diverse applications. Its unique structure and properties make it a valuable component in the synthesis of various chemical products.

InChI:InChI=1/C13H11N3O3/c17-13(14-10-5-2-1-3-6-10)15-11-7-4-8-12(9-11)16(18)19/h1-9H,(H2,14,15,17)

Upstream product

• 13140-66-4 1-(3-nitrophenyl)-3-phenylthiourea 
• 103-71-9 phenyl isocyanate 
• 99-09-2 3-nitro-aniline 
• 3320-87-4 isocyanic acid (3-nitro-phenyl) ester 
• 62-53-3 aniline 
• 108-88-3 toluene 
• 71-43-2 benzene 
• 101-99-5 N-carboethoxyaniline 
• 7664-93-9 sulfuric acid 
• 33322-43-9 3-nitro-benzoic acid bromoamide 
• 99-65-0 meta-dinitrobenzene 
• 618-94-0 3-nitrobenzoic acid hydrazide 
• 103-72-0 phenyl isothiocyanate 
• 3532-31-8 3-nitrobenzoyl azide 

Downstream Products

• 1194230-73-3 N,N'-di-n-propyl-N-phenyl-N'-(3-nitrophenyl)urea 
• 13140-79-9 1,1'-(1,3-phenylene)bis(3-phenylurea) 
• 1192928-25-8 3,4,5-trimethoxy-N-(3-(3-phenylureido)phenylcarbamothioyl)benzamide 
• 66695-96-3 N-(3-aminophenyl)-N'-phenylurea 

Relevant academic research and scientific papers

Synthesis of new phenolic compounds and biological evaluation as antiproliferative agents

New series of phenolic azomethine compounds in addition to 5-arylidene thiazolidinones are synthesized and screened for their anticancer activity against the brain cancer cell line SNB-75 and non-small lung cancer cells HOP-92. The azomethine derivative 12b is the most active compound against SNB-75 displaying an IC50 value of 0.14 μM. Compounds 7b, 16a and 27d display submicromolar activity against the HOP-92 cell line with IC50 values of 0.73, 0.74 and 0.81 μM, respectively. Moreover, studying the cytotoxic effects of the most active compounds against normal lung cells WI-38 revealed that compounds 7b, 16a and 27d showed high safety profiles as anticancer agents.

Probing 2H-Indazoles as Templates for SGK1, Tie2, and SRC Kinase Inhibitors

The broader and systematic application of a novel scaffold is often hampered by the unavailability of a short and reliable synthetic access. We investigated a new strategy for the design and synthesis of an array of N2-substituted aza-2H-indazole derivatives as potential kinase inhibitors. Guided by a rational ligand alignment approach to qualify the so-far underrepresented aza-2H-indazole scaffold, indazoles were connected at the N2 position with a phenyl spacer and an arylsulfonamide or amide linkage. Initial profiling against a panel of 30 kinases confirmed the in silico predicted selectivity bias. A synthesized focused library of 52 different aza-2H-indazole derivatives showed good initial selective inhibition against SGK1, Tie2, and SRC kinases, with the best representatives having IC50 values in the range of 500 nm. In a comparative computational study, these data were analyzed and rationalized in light of docking studies.

Mechanochemical catalytic transfer hydrogenation of aromatic nitro derivatives

Mechanochemical ball milling catalytic transfer hydrogenation (CTH) of aromatic nitro compounds using readily available and cheap ammonium formate as the hydrogen source is demonstrated as a simple, facile and clean approach for the synthesis of substituted anilines and selected pharmaceutically relevant compounds. The scope of mechanochemical CTH is broad, as the reduction conditions tolerate various functionalities, for example nitro, amino, hydroxy, carbonyl, amide, urea, amino acid and heterocyclic. The presented methodology was also successfully integrated with other types of chemical reactions previously carried out mechanochemically, such as amide bond formation by coupling amines with acyl chlorides or anhydrides and click-type coupling reactions between amines and iso(thio)cyanates. In this way, we showed that active pharmaceutical ingredients Procainamide and Paracetamol could be synthesized from the respective nitro-precursors on milligram and gram scale in excellent isolated yields.

Halogen-substituted ureas for anion binding: solid state and solution studies

Herein, we report the synthesis and the anion binding properties of a family of N,N′-diphenylureas L1-L15, bearing on the aromatic ring(s) halogens (chlorine and iodine) and/or nitro or trifluoromethyl electron-withdrawing groups. The analysis of the crystal structures obtained from single crystal X-ray diffraction experiments shows that self-assembled chains or tapes connected via N–H···O hydrogen bonds are the most commonly adopted arrangements for this type of molecules in the crystal lattice. In the presence of anion guests or solvent molecules with competing hydrogen bond donors and acceptors, other supramolecular arrangements can be observed. Solution studies conducted in DMSO-d6/0.5% H2O by means of 1H-NMR titrations show the formation of 1:1 adducts with all receptors. The different observed affinities of the receptors for the anion guests were rationalised in terms of steric hindrance of the substituents on the phenyl rings and their electron-withdrawing properties.

Functional foldamers that target bacterial membranes: The effect of charge, amphiphilicity and conformation

By varying the molecular charge, shape and amphiphilicity of a series of conformationally distinct diarylureas it is possible to control the levels of phospholipid membrane lysis using membranes composed of bacterial lipid extracts. From the data obtained, it appears as though the lysis activity observed is not due to charge, conformation or amphiphilicity in isolation, but that surface aggregation, H-bonding and other factors may also play a part. The work provides evidence that this class of foldamer possesses potential for optimisation into new antibacterial agents.

NMR method for simultaneous host-guest binding constant measurement

An NMR-based relative binding affinity measurement method has been developed in which differences in the binding affinities of different hosts toward a particular guest (ΔlogKass values) are measured in the same solution. As an advancement, the

Synthesis and helical properties of aromatic multilayered oligoureas

Several aromatic multilayered oligoureas with different chain lengths and different numbers of chiral N-substituents were synthesized, and their helical conformation and induced handedness were examined by means of CD spectroscopy. Introduction of one chi

Identification of absolute helical structures of aromatic multilayered oligo(m-phenylurea)s in solution

(Chemical Equation Presented) The oligomeric aromatic ureas bearing N,N′-dimethylated urea bonds such as 3 have aromatic multi-layered structure, based on the (cis,cis)-urea structure, and also have dynamic helical structure (all-R or all-S axis chirality) when the benzene rings are connected at the meta positions. The absolute helical structure of oligo(m-phenylurea)s were identified by the empirical and theoretical studies on the CD and vibrational CD (VCD) spectra. Thus, each enantiomer of the oligo(m-phenylurea)s 4 bearing a chiral N-2-(methoxyethoxyethoxy)propyl group were synthesized. Intense dispersion-type CD spectra of 4 were observed, which indicated the induction of handedness in the helical structure. In the VCD spectra of 4 in the film state, the signals due to the carbonyl and aromatic ring vibrations were seen with negative and positive values for compounds 4a and 4b, respectively. The calculations of both CD and VCD spectra of oligo(m-phenylurea)s 3 without any chiral N-substituent gave the same assignment about the axis chirality of 4. Thus, the absolute configurations of 4a and 4b are all-R and all-S structures, respectively. 2009 American Chemical Society.

Unsymmetrically disubstituted urea derivatives: A potent class of antiglycating agents

A series of unsymmetrically disubstituted urea derivatives 1-28 has been synthesized and screened for their antiglycation activity in vitro. Compounds 26 (IC50 = 4.26 ± 0.25 μM), 1 (IC50 = 5.8 ± 0.08 μM), 22 (IC50 = 4.26 ± 0.25 μM), 6 (IC50 = 6.4 ± 0.02 μM), 5 (IC50 = 6.6 ± 0.26 μM), 2 (IC50 = 7.02 ± 0.31 μM), 3 (IC50 = 7.14 ± 0.84 μM), 27 (IC50 = 7.27 ± 0.36 μM), 4 (IC50 = 8.16 ± 1.04 μM), 21 (IC50 = 8.4 ± 0.15 μM), 23 (IC50 = 9.0 ± 0.35 μM) and 13 (IC50 = 15.22 ± 6.7 μM) showed an excellent antiglycation activity far better than the standard (rutin, IC50 = 41.9 ± 2.3 μM). This study thus provides a series of potential molecules for further studies of antiglycation agents.

Synthesis and activity evaluation of phenylurea derivatives as potent antitumor agents

We have discovered several tubulin-active compounds in our previous studies. In the establishment of a compound library of small molecule weight tubulin ligands, 14 new N-3-haloacylaminophenyl-N′-(alkyl/aryl) urea analogs were designed and synthesized. The structure-activity relationship (SAR) analysis revealed that (i) the order of anticancer potency for the 3-haloacylamino chain was following -CH2Br > -CHBrCH3; (ii) the N′-substituent moiety was not essential for the anticancer activity, and a proper alkyl substitution might enhance the anticancer activity. Among these analogs, the compounds 16j bearing bromoacetyl at the N′-end exhibited a potent activity against eight human tumor cell lines, including CEM (leukemia), Daudi (lymphoma), MCF-7 (breast cancer), Bel-7402 (hepatoma), DU-145 (prostate cancer), DND-1A (melanoma), LOVO (colon cancer) and MIA Paca (pancreatic cancer), with the IC50 values between 0.38 and 4.07 μM. Interestingly, compound 16j killed cancer cells with a mechanism independent of the tubulin-based mechanism, indicating a significant change of the action mode after the structure modification.