7669-49-0

Usage

Uses

Used in Organic Synthesis:
1-(4-Nitrophenyl)-3-phenyl-2-thiourea is used as an organic intermediate for the synthesis of other chemicals. Its unique structure and properties make it a valuable component in the creation of various chemical compounds.
Used in Pharmaceutical Industry:
1-(4-Nitrophenyl)-3-phenyl-2-thiourea is used as a pharmaceutical intermediate for the development of new drugs. Its biological activities, such as anti-inflammatory and antioxidant properties, contribute to its potential use in the treatment of various diseases and conditions.
Used in Antiparasitic Applications:
1-(4-Nitrophenyl)-3-phenyl-2-thiourea is studied for its potential use as an antiparasitic agent. Its ability to target and eliminate parasites makes it a promising candidate for the development of new antiparasitic drugs.

InChI:InChI=1/C13H11N3O2S/c17-16(18)12-8-6-11(7-9-12)15-13(19)14-10-4-2-1-3-5-10/h1-9H,(H2,14,15,19)

Upstream product

• 103-72-0 phenyl isothiocyanate 
• 785-81-9 4-nitro-N-(phenylmethylene)benzenamine 
• 62-53-3 aniline 
• 2131-61-5 p-nitrophenyl isothiocyanate 
• 72995-55-2 2-tert-butyl-4-(4-nitro-phenyl)-3-phenyl-[1,2,4]oxadiazolidine-5-thione 
• 100-01-6 4-nitro-aniline 
• 75305-28-1 4-Nitro-N-[1-phenyl-1-(3-phenyl-thioureido)-meth-(Z)-ylidene]-benzenesulfonamide 
• 74439-49-9 C₁₄H₉N₃O₄S₂ 
• 2420-60-2 O-phenyl N-(4-nitrophenyl)thiocarbamate 

Downstream Products

• 7669-27-4 [3-(4-nitro-phenyl)-4-oxo-2-phenylimino-thiazolidin-5-yl]-acetic acid 
• 58151-18-1 [3-(4-nitro-phenyl)-[1,3]thiazetidin-2-ylidene]-phenyl-amine 
• 65672-94-8 (4-nitro-phenyl)-(3-phenyl-[1,3]thiazetidin-2-ylidene)-amine 
• 54568-24-0 (3-amino-4-phenyl-4H-[1,2,4]thiadiazol-5-ylidene)-(4-nitro-phenyl)-amine 
• 111022-26-5 1-(4-Nitro-phenyl)-3-phenyl-thiourea; compound with 2,3-dicyano-but-2-enedinitrile 
• 3111-89-5 O-ethyl-N-phenylthiocarbamate 
• 13806-75-2 N-(4-nitrophenyl)thiocarbamic acid O-ethyl ester 
• 102-08-9 N,N-diphenylthiourea 
• 18440-30-7 N,N',N''-tris-(4-nitro-phenyl)-guanidine 
• 100-01-6 4-nitro-aniline 
• 1010-53-3 3-phenyl-2,4-thiazolidinedione 
• 114710-79-1 2-[(Z)-4-Nitro-phenylimino]-3-phenyl-thiazolidin-4-one 
• 66695-94-1 1–(4-aminophenyl)-3-phenylthiourea 
• 636-04-4 N-Phenylbenzothioamide 

Relevant academic research and scientific papers

Selective binding and extraction of aqueous dihydrogen phosphate solutions via three-armed thiourea receptors

A series of neutral anion receptors with one to three thiourea arms were synthesized and their binding to tetrabutylammonium chloride, acetate, and dihydrogen phosphate salts in aqueous DMSO mixtures was examined. The three-armed thiourea host was found to strongly and selectively bind H2PO4- even in DMSO solutions containing up to 30% water. This enabled the dihydrogen phosphate salt to be extracted from water into chloroform in its dibasic form despite the high heat of the hydration of HPO42-.

Molecular design, synthesis and in vitro biological evaluation of thienopyrimidine–hydroxamic acids as chimeric kinase HDAC inhibitors: a challenging approach to combat cancer

A series of thieno[2,3-d]pyrimidine-based hydroxamic acid hybrids was designed and synthesised as multitarget anti-cancer agents, through incorporating the pharmacophore of EGFR, VEGFR2 into the inhibitory functionality of HDAC6. Three compounds (12c, 15b and 20b) were promising hits, whereas (12c) exhibited potent VEGFR2 inhibition (IC50=185 nM), potent EGFR inhibition (IC50=1.14 μM), and mild HDAC6 inhibition (23% inhibition). Moreover, compound (15c) was the most potent dual inhibitor among all the synthesised compounds, as it exhibited potent EGFR and VEGFR2 inhibition (IC50=19 nM) and (IC50=5.58 μM), respectively. While compounds (20d) and (7c) displayed nanomolar selective kinase inhibition with EGFR IC50= 68 nM and VEGFR2 IC50= 191 nM, respectively. All of the synthesised compounds were screened in vitro for their cytotoxic effect on 60 human NCI tumour cell lines. Additionally, molecular docking studies and ADMET studies were carried out to gain further insight into their binding mode and predict the pharmacokinetic properties of all the synthesised inhibitors.

Hydroamination and Hydrophosphination of Isocyanates/Isothiocyanates under Catalyst-Free Conditions

Symmetrical and unsymmetrical N,N’-disubstituted as well as trisubstituted ureas/thioureas by the hydroamination of isocyanates/isothiocyanates, and various phosphathioureas by the hydrophosphination of isothiocyanates have been synthesized in good to excellent yields under catalyst-free and mild conditions. This protocol is also applicable for the efficient synthesis of chiral ureas and thioureas and common herbicides, such as fenuron and monuron.

Tunable NIR-II emitting silver chalcogenide quantum dots using thio/selenourea precursors: Preparation of an MRI/NIR-II multimodal imaging agent

Aqueous-stable, Cd- and Pb-free colloidal quantum dots with fluorescence properties in the second near-infrared region (NIR-II, 1000-1400) are highly desirable for non-invasive deep-tissue optical imaging and biosensing. The low band-gap semiconductor, silver chalcogenide, offers a non-toxic and stable alternative to existing Pd, As, Hg and Cd-based NIR-II colloidal quantum dots (QDs). We report facile access to NIR-II emission windows with Ag2X (X = S, Se) QDs using easy-to-prepare thio/selenourea precursors and their analogues. The aqueous phase transfer of these QDs with a high conservation of fluorescence quantum yield (retention up to ～90%) and colloidal stability is demonstrated. A bimodal NIR-II/MRI contrast agent with a tunable fluorescence and high T1 relaxivity of 408 mM-1 s-1 per QD (size ～ 2.2 nm) and 990 mM-1 s-1 per QD (size ～ 4.2 nm) has been prepared by grafting 50 and 120 monoaqua Gd(iii) complexes respectively to two differently sized Ag2S QDs. The size of the nanocrystals is crucial for tuning the Gd payload and the relaxivity.

Hydrogen-Bond Catalysis of Imine Exchange in Dynamic Covalent Systems

The reversibility of imine bonds has been exploited to great effect in the field of dynamic covalent chemistry, with applications such as preparation of functional systems, dynamic materials, molecular machines, and covalent organic frameworks. However, acid catalysis is commonly needed for efficient equilibration of imine mixtures. Herein, it is demonstrated that hydrogen bond donors such as thioureas and squaramides can catalyze the equilibration of dynamic imine systems under unprecedentedly mild conditions. Catalysis occurs in a range of solvents and in the presence of many sensitive additives, showing moderate to good rate accelerations for both imine metathesis and transimination with amines, hydrazines, and hydroxylamines. Furthermore, the catalyst proved simple to immobilize, introducing both reusability and extended control of the equilibration process.

Design, synthesis and molecular modeling study of certain VEGFR-2 inhibitors based on thienopyrimidne scaffold as cancer targeting agents

Different series of novel thieno [2,3-d]pyrimidine derivative (9a-d,10a-f,l,m and 15a-m) were designed, synthesized and evaluated for their ability to in vitro inhibit VEGFR-2 enzyme. Also, the cytotoxicity of the final compounds was tested against a panel of 60 different human cancer cell lines by NCI. The VEGFR-2 enzyme inhibitory results revealed that compounds 10d, 15d and 15 g are among the most active inhibitors with IC50 values of 2.5, 5.48 and 2.27 μM respectively, while compound 10a remarkably showed the highest cell growth inhibition with mean growth inhibition (GI) percent of 31.57%. It exhibited broad spectrum anti-proliferative activity against several NCI cell lines specifically on human breast cancer (T7-47D) and renal cancer (A498) cell lines of 85.5% and 77.65% inhibition respectively. To investigate the mechanistic aspects underlying the activity, further biological studies like flow cytometry cell cycle together with caspase-3 colorimetric assays were carried on compound 10a. Flow cytometric analysis on both MCV-7 and PC-3 cancer cells revealed that it induced cell-cycle arrest in the G0-G1phase and reinforced apoptosis via activation of caspase-3. Furthermore, molecular modeling studies have been carried out to gain further understanding of the binding mode in the active site of VEGFR-2 enzyme and predict pharmacokinetic properties of all the synthesized inhibitors.

Dual roles of substituted thiourea as reductant and ligand in CuAAC reaction

A highly efficient catalytic system, CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea, for the copper(I)-catalyzed azide–alkyne cycloaddition reaction (CuAAC) was discovered. In the above catalytic system, substituted thiourea acts both as a reductant and a ligand. CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea is both an economical and efficient catalyst for the CuAAC reaction. In addition, the new catalytic system has advantageous features including mild and green reaction conditions, and broad substrate compatibility. A variety of 1,4-disubstituted 1,2,3-triazoles have been prepared with good to excellent yields with the CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea catalytic system in aqueous solution.

Hydroamination of carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(IV) complex

The hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(iv) complex as a precatalyst is reported here. The titanium(iv) complex [{Ph2P(Se)NCH2CH2NPPh2(Se)}Ti(NMe2)2] (1) was synthesised by the reaction of tetrakis-(dimethylamido)titanium(iv) [Ti(NMe2)4] with [{Ph2P(Se)NHCH2CH2NHPPh2(Se)}] in toluene at ambient temperature. Titanium complex 1 proved to be a competent pre-catalyst for the addition of an amine N-H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanates and phenylisothiocyanates in toluene solvents proceeding rapidly at room temperature with 5 mol% catalyst loadings to yield the corresponding urea and thio-urea derivatives up to 99%. However, ambient temperature was needed for hydroamination of 1,3-dicyclohexylcarbodiimide. The amine addition reactions with isocyanates showed first order kinetics with respect to catalyst 1 as well as substrates. The most plausible mechanism for the hydroamination reaction was established by isolating 1,1-dimethylphenyl urea as a side product.

Cooperative binding and extraction of sodium nitrite by a ditopic receptor incorporated into a polymeric resin

Simple ion pair receptors were synthesised and characterized in solution. The modular design of these receptors facilitated the preparation of a functionally analogous polymeric material able to extract sodium nitrite from acetonitrile solution.

Convenient synthesis of unsymmetrical N,N′-disubstituted thioureas in water

A simple and convenient two-step method has been developed and used to synthesise 25 (4 of which are novel) unsymmetrical N,N′-disubstituted thioureas in water. Alkylamines or variously substituted arylamines reacted smoothly with phenyl chlorothionoformate at room temperature to form thiocarbamates, which were then reacted with another alkyl- or arylamine in water at reflux to afford the unsymmetrical N,N′-disubstituted thioureas in good to excellent yields. Mild conditions, simple work-up, high yields as well as using water as solvent are the major advantages of the method.