5467-04-9

Usage

Uses

Used in Research and Pharmaceutical Industries:
N,N'-(p-Phenylene)bisbenzamide is used as a coupling reagent for the synthesis of peptides, facilitating the formation of peptide bonds which is crucial in the development of new drugs and therapeutic agents.
Used in Protein Kinase C Inhibition:
N,N'-(p-Phenylene)bisbenzamide is used as an inhibitor of protein kinase C, a key enzyme involved in various cellular processes. Its potential therapeutic properties make it valuable in the development of treatments for diseases where protein kinase C plays a significant role.

Upstream product

• 98-88-4 benzoyl chloride 
• 106-50-3 1,4-phenylenediamine 
• 10364-94-0 1-benzoylimidazole 
• 624-18-0 benzene-1,4-diamine hydrochloride 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 93-97-0 benzoic acid anhydride 
• 65-85-0 benzoic acid 
• 17625-83-1 N-(4-aminophenyl)benzamide 
• 16720-35-7 N,N'-2,5-cyclohexadiene-1,4-diylidenebis 
• 64-19-7 acetic acid 
• 100-51-6 benzyl alcohol 
• 110-89-4 piperidine 

Downstream Products

• 15999-99-2 N,N'-p-phenylene-bis-benzimidoyl chloride 
• 66012-79-1 5,5'-diphenyl-1H,1'H-1,1'-p-phenylene-bis-tetrazole 
• 43036-58-4 2,6-diphenylbenzo[1,2-d:4,5-d']bis(oxazole) 
• 1237477-92-7 (Z,Z)-N,N'-(p-phenylene)dibenzimidoyl dichloride 
• 1237477-96-1 N,N'-bis[(diphenylphosphoryl)phenylmethylidene]-1,4-benzenediamine 
• 1237477-97-2 C₂₈H₃₄N₂O₆P₂ 
• 1237477-99-4 C₃₂H₄₅N₂O₉P₃ 
• 1237478-02-2 C₃₆H₅₆N₂O₁₂P₄ 
• 314751-39-8 N,N'-(2,6-dichloro-p-phenylene)-bis-benzamide 
• 102160-68-9 N,N'-(2,5-dichloro-p-phenylene)-bis-benzamide 
• 308291-66-9 N,N'-dibenzoyl-2,6-dichloro-1,4-benzoquinone diimine 
• 24118-33-0 2,5-bis-benzoylamino-[1,4]benzoquinone 
• 16000-05-8 N,N'-(p-Phenylen)-bis-benzimidsaeure-bis-(4-benzolazo-2-methoxycarbonyl-phenylester) 

Relevant academic research and scientific papers

Insight into Fundamental Rules of Phenylenediamines Selective Monoacylation by the Comparisons of Kinetic Characteristics in Microreactor

In this paper, the kinetics of acylation reaction of o-phenylenediamine/p-phenylenediamine and benzoic anhydride were determined in microreactors, respectively. A kinetic model was established, all kinetic parameters including reaction orders, reaction rate constants, pre-exponential factors, and activation energies were acquired. Validation experiments showed experimental data fit well with calculated data at different reactant concentrations and residence times. The comparisons of the reaction rate constants and activation energies were summarized to show the difference of chemical reactivities of phenylenediamines. According to the calculation of the kinetic model, the optimized reaction conditions were listed to meet the monoacylation selectivity equal to 97.0%.

Amide derivatives of Gallic acid: Design, synthesis and evaluation of inhibitory activities against in vitro α-synuclein aggregation

Gallic acid (GA), a natural phenolic acid, has received numerous attention because of its anti-oxidative, anti-inflammatory, and anti-cancer activity. More importantly, GA can act as an efficient inhibitor of α-Synuclein (α-Syn) aggregation at early stages. Nevertheless, some evidences suggest that GA is unlikely to cross the blood–brain barrier because of its high hydrophilicity. Hence, GA may not be considered as a promising candidate or entering brain and directly affecting the central nervous system. Accordingly, we have designed and synthesized a series of amide derivatives of GA, some of which possess appropriate lipophilicity and hydrophilicity with LogP (2.09–2.79). Meanwhile, these sheet-like conjugated compounds have good π-electron delocalization and high ability of hydrogen-bond formation. Some compounds have shown better in vitro anti-aggregation activities than GA towards α-Syn, with IC50 down to 0.98 μM. The valid modification strategy of GA is considered an efficient way to discover novel inhibitors of α-Syn aggregation.

One-step synthesis of dicarboxamides through Pd-catalysed aminocarbonylation with diamines as N-nucleophiles

An efficient one-step synthetic strategy was used to prepare a set of dicarboxamides through palladium-catalysed aminocarbonylation of iodoalkenyl and iodoaryl compounds, with use of various alkyl- and aryldiamines as N-nucleophiles. The isolated yields of the dicarboxamides depended significantly on the iodo substrate and diamine structures, as well as on the reaction conditions, the best one (ca. 70%) being achieved with 1-iodocyclohexene as substrate and 1,4-diaminobutane as nucleophile, at 100°C and 30 bar of CO. When iodobenzene was used as model aryl halide, the highest yield of the target dibenzamides (ca. 65%) was obtained with 1,4-diaminobenzene as coupling amine, at 100°C and 10 bar of CO. Preliminary studies on their in vitro cytotoxicity against human lung carcinoma A549 cells showed N,N′(butane-1,4-diyl)dibenzamide and androst-16-ene-based dicarboxamides to be the most efficient cytotoxic agents, with IC50 values of approximately 40 μM.

Reaction of N,N′-disubstituted 1,4-benzoquinone diimines with sodium arenesulfinates

Radical anion 1,6-addition path in the reactions of N,N′-disubstituted 1,4-benzoquinone diimines with sodium arenesulfinates is favored by increase of the electron-donating power of the substituent in the para position of arenesulfinate ion and redox pote

Probing the intermolecular interactions of aromatic amides containing N-heterocycles and triptycene

A series of aromatic amides incorporated with N-heterocycles or triptycene units are synthesized and studied for probing the effects of such chemical modifications on the intermolecular interactions. Single crystals of a number of heterocyclic amides and the triptycene-containing amide were obtained. Crystal structures, hydrogen bonds, lattice energy, solubility, and melting points were compared amongst relevant molecules. Suitably positioned nitrogen atoms from heterocycles are found to form intramolecular H-bonds with amide NHs at the expense of weakening or disrupting the intermolecular H-bonds. The effects of such H-bonding changes on solubility and melting point are nonetheless limited. Uniquely, the triptycene unit effectively improves the solubility of the amide without tempering the thermal resistance of the molecule. This journal is the Partner Organisations 2014.

Amidation of aromatic amine and benzoic acid under boric acid catalysis

Synthesis of amides from the condensation reactions between aromatic amines and benzoic acids in the presence of boric acid is described. Aromatic amines include aniline 1,3-phenylenediamine and 1,4-phenylenediamine. Results indicate that the dehydrative amide procedure can be catalyzed by boric acid under mild conditions. The reaction is simple and the catalyst is readily available.

Direct synthesis of amides from coupling of alcohols and amines catalyzed by ruthenium(II) thiocarboxamide complexes under aerobic conditions

Four octahedral ruthenium(II) thiocarboxamide complexes of the general formula [RuClCO(AsPh3)2(L)] (L = N-substituted pyridine-2-thiocarboxamide) incorporating carbonyl and triphenylarsine have been synthesized from the reaction of 1 equiv of ruthenium precursor [RuHClCO(AsPh3)3] with 1 equiv of thiocarboxamide ligands in refluxing ethanol in the presence of base. All the new complexes have been fully characterized by means of elemental analysis, IR, UV-vis, and NMR spectral methods. Molecular structures of all the complexes were determined by X-ray crystallography, which confirm the coordination mode of thiocarboxamide and reveal the presence of a distorted octahedral geometry around the Ru ion. All the ruthenium(II) thiocarboxamide complexes were generated as highly efficient catalysts for synthesis of secondary or tertiary amides by coupling of amines and alcohols with low catalyst loading, and the maximum yield was obtained up to 97%. The coupling reaction can be readily carried out under mild aerobic conditions, and release of water is the only byproduct. Further, the effect of substituents of the ligand, solvents, reaction temperature, time, and catalyst loading on the catalytic activity of the complexes has been investigated. A plausible mechanism is proposed for the synthesis of amides via hemiaminal as intermediate through an oxidation of an alcohol to aldehyde.

Imidazole-catalyzed monoacylation of symmetrical diamines

Figure Presented. An imidazole-catalyzed protocol for monoacylation of symmetrical diamines has been developed. The protocol gave selective monoacylation of aliphatic (cyclic and acyclic) primary and secondary diamines. In the reaction, imidazole acts as both catalyst and a leaving group. Different monoacylated piperazines and other diamines were synthesized at room temperature in an ethanol/water solvent system.

Bisphosphorylated ligands based on isomeric N,N'-phenylenedibenzimidoyl dichlorides

The Arbuzov reaction of N,N'-phenylenedibenzimidoyl dichlorides furnished new tet radentate ligands, viz., N,N'-bis[(diphenylphosphoryl)phenylmethylidene] benzenediamines, which form complexes with lanthanides.

Chemoselective acylation of amines in aqueous media

Amines are efficiently acylated by both cyclic and acyclic anhydrides by dissolving them in an aqueous medium with the help of a surfactant, sodium dodecyl sulfate (SDS). Cyclic and acyclic anhydrides react with equal ease with an amine, and amines with various stereo-electronic factors react at the same rates with an anhydride. Chemoselective acylation of amines in the presence of phenols and thiols and of thiols in the presence of phenols has been achieved. No acidic or basic reagents are used during the reaction. No Chromatographic separation is required for isolation of the acylated products. Reactions in a neutral aqueous medium, easy isolation of products, and innocuous by-products make the present method a green chemical process. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.