14315-16-3

Usage

Uses

Used in Scientific Research:
3-Aminobenzanilide is used as a chemical intermediate for the synthesis of various organic compounds and pharmaceuticals. Its unique structure allows it to be a versatile building block in the development of new molecules with potential applications in different fields.
Used in Pharmaceutical Industry:
3-Aminobenzanilide is used as a key component in the synthesis of certain drugs, particularly those targeting specific biological pathways. Its presence in the molecular structure can influence the drug's activity, selectivity, and potency, making it an important player in drug discovery and development.
Used in Chemical Synthesis:
3-Aminobenzanilide is used as a reagent in various chemical reactions, such as condensation, substitution, and rearrangement reactions. Its ability to participate in these reactions makes it a valuable tool for chemists in creating new compounds with desired properties and applications.

InChI:InChI=1/C13H12N2O/c14-11-6-4-5-10(9-11)13(16)15-12-7-2-1-3-8-12/h1-9H,14H2,(H,15,16)

Upstream product

• 2243-73-4 5-nitrobenzanilide 
• 99-05-8 meta-aminobenzoic acid 
• 62-53-3 aniline 
• 7664-93-9 sulfuric acid 
• 874337-73-2 C₁₈H₂₀N₂O₃ 
• 21563-72-4 3-Aminobenzoyl chloride 
• 121-90-4 m-nitrobenzoic acid chloride 
• 15151-51-6 3-aminobenzoic acid hydrochloride 
• 121-92-6 3-nitrobenzoic acid 
• 111331-82-9 3-[(tert-butoxycarbonyl)amino]benzoic acid 

Downstream Products

• 55251-28-0 3-Trifluoromethansulfonamidobenzanilid 
• 90233-67-3 N-Phenyl-3-(pyrrolidine-1-sulfonylamino)-benzamide 
• 90233-68-4 N-Phenyl-3-(piperidine-1-sulfonylamino)-benzamide 
• 90233-73-1 N-Phenyl-3-(propane-2-sulfonylamino)-benzamide 
• 90233-69-5 3-Methanesulfonylamino-N-phenyl-benzamide 
• 874337-76-5 diethyl ({[3-(anilinocarbonyl)phenyl]amino}methylene)malonate 
• 90233-70-8 3-Benzenesulfonylamino-N-phenyl-benzamide 
• 1400659-69-9 C₁₆H₁₅FN₂O₂ 
• 1395923-49-5 C₂₄H₂₂N₂O₂ 

Relevant academic research and scientific papers

Electrochemical: N-acylation synthesis of amides under aqueous conditions

An electrochemical N-acylation of carboxylic acids with amines was reported. The sustainable TBAB electrocatalysis proceeded with excellent chemoselectivity and positional selectivity, and with ample scope, allowing electrochemical N-acylation under mild reaction conditions at room temperature in water. Moreover, the synthetic utility of the current method is demonstrated by the synthesis of melatonin.

Fragmentation of Protonated N-(3-Aminophenyl)Benzamide and Its Derivatives in Gas Phase

An ion of m/z 110.06036 (ion formula [C6H8NO]+; error: 0.32 mDa) was observed in the collision induced dissociation tandem mass spectrometry experiments of protonated N-(3-aminophenyl)benzamide, which is a rearrangement product ion purportedly through nitrogen-oxygen (N–O) exchange. The N–O exchange rearrangement was confirmed by the MS/MS spectrum of protonated N-(3-aminophenyl)-O18-benzamide, where the rearranged ion, [C6H8NO18]+ of m/z 112 was available because of the presence of O18. Theoretical calculations using Density Functional Theory (DFT) at B3LYP/6-31?g(d) level suggest that an ion-neutral complex containing a water molecule and a nitrilium ion was formed via a transition state (TS-1), followed by the water molecule migrating to the anilide ring, eventually leading to the formation of the rearranged ion of m/z 110. The rearrangement can be generalized to other protonated amide compounds with electron-donating groups at the meta position, such as, –OH, –CH3, –OCH3, –NH(CH3)2, –NH-Ph, and –NHCOCH3, all of which show the corresponding rearranged ions in MS/MS spectra. However, the protonated amide compounds containing electron-withdrawing groups, including –Cl, –Br, –CN, –NO2, and –CF3, at the meta position did not display this type of rearrangement during dissociation. Additionally, effects of various acyl groups on the rearrangement were investigated. It was found that the rearrangement can be enhanced by substitution on the ring of the benzoyl with electron-withdrawing groups. [Figure not available: see fulltext.]

HUMAN PLASMA KALLIKREIN INHIBITORS

Disclosed are compounds of formula (I), as described herein, and pharmaceutically acceptable salts thereof. The compounds are inhibitors of plasma kallikrein. Also provided are pharmaceutical compositions comprising at least one compound of the invention, and methods involving use of the compounds and compositions of the invention in the treatment and prevention of diseases and conditions characterized by unwanted plasma kallikrein activity.

Synthesis and antiviral activity of substituted bisaryl amide compounds as novel influenza virus inhibitors

The influenza virus is a persistent cause of mortality and morbidity on an annual basis and thus presents itself as an important target for pharmaceutical investigation. In this work, substituted bisaryl amide compounds were found to be a new class of potential anti-influenza agents, and a series of substituted bisaryl amide compounds were synthesised and evaluated for their anti-influenza virus activities. The analysis of the results produced a preliminary structure-activity relationship study (SAR). Compounds 1a, 1g, 1h, 1j, 1l and 1n exhibited clear antiviral activities against the influenza A (A/Guangdong Luohu/219/2006, H1N1) virus with 50% inhibitory concentrations (IC50) for virus growth ranging from 12.5 to 59.0 μM. Specifically, compound 1j also possessed antiviral activity against both oseltamivir-resistant influenza (A/Jinnan/15/2009) virus and influenza B (B/Jifang/13/97) virus with IC 50 values of 9.2 μM and 21.4 μM, respectively. Compound 1j is thus worth further investigation as an anti-influenza virus candidate.

Synthesis, catalytic activity, and photophysical properties of 5,6-membered Pd and Pt SCS′-pincer complexes based on thiophosphorylated 3-amino(hydroxy)benzoic acid thioanilides

Novel unsymmetrical SCS′-pincer ligands, 1-[PhNHC(S)]-3-[Ph 2P(S)NH]-C6H4 (3) and 1-[PhNHC(S)]-3-[Ph 2P(S)O]C6H4 (7), bearing a thiocarbamoyl moiety in combination with thiophosphorylamino- and thiophosphoryloxy-donating groups, respectively, were obtained via thiophosphorylation of 3-amino- and 3-hydroxy-benzoic acid (thio)anilides 1 and 6. Direct cyclometallation of the central benzene ring in the ligands 3 and 7 in reaction with (PhCN) 2MCl2 (M = Pd, Pt) as a metal precursor afforded κ3-SCS′-hybrid pincer complexes 8, 9 with 5- and 6-membered fused metallacycles in good to high yields (67-95%). The complexes 8 and 9 were characterized by multinuclear NMR (31P, 1H, 13C) and IR spectroscopy as well as single-crystal X-ray crystallography. Palladium complexes 8a and 9a were shown to be active catalysts for the Suzuki-Miyaura cross-coupling reaction. In the solid state the ligands 3 and 7 as well as their Pt(ii) and Pd(ii) complexes 8 and 9 are luminescent at 300 K. The emission of the complexes has the different origin depending on the metal nature.

ARYL CARBOXAMIDE DERIVATIVES AS SODIUM CHANNEL INHIBITORS FOR TREATMENT OF PAIN

The present invention provides compounds that are inhibitors of voltage-gated sodium channels (Nav), in particular Nav 1.7, and are therefore useful for the treatment of diseases treatable by inhibition of these channels, in particular, chronic pain disorders. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

Thiophosphoryl-, thiophosphoryloxy-, and thiophosphorylamino-benzene derivatives as novel classes of hybrid pincer ligands

The synthetic approaches to novel families of SCE (E = S',N,O) hybrid pincertype ligands bearing thophosphoryl, thiophosphoryloxy, and thiophosphorylamino groups in various combinations with thiophosphoryl-, thiocarbamoyl-, and imine- (including that of benzothiazole ring) donating functions have been developed. All of the ligands readily undergo direct cyclometallation (metal = Pd(II), Pt(II)) to afford 5,5- or 5,6-membered pincer complexes. Palladium complexes displayed from high to excellent catalytic performance in the Suzuki cross-coupling reaction of aryl bromides and phenylboronic acid and the higher asymmetry for a complex served as a factor of its higher catalytic activity. Copyright Taylor & Francis Group, LLC.

Selective reduction of aromatic nitro groups in the presence of amide functionality

Pressure mediated selective reduction of aromatic nitro groups in the presence of amide functionality has been achieved by use of hydrazine hydrate.

The inhibition of factor inhibiting hypoxia-inducible factor (FIH) by β-oxocarboxylic acids

Cyclic β-oxocarboxylic acids inhibit factor inhibiting hypoxia-inducible factor via ligation to the active site iron. The Royal Society of Chemistry 2005.

Use of glycogen phosphorylase inhibitors

The invention provides methods of treating prophylactically an individual in whom Type 2 diabetes mellitus has not yet presented, but in whom there is an increased risk of developing such condition, which methods comprise administering to an individual in need thereof an effective amount of a glycogen phosphorylase inhibitor; effective amounts of a glycogen phosphorylase inhibitor and a non-glycogen phosphorylase inhibiting anti-diabetic agent; or effective amounts of a glycogen phosphorylase inhibitor and an anti-obesity agent. The invention further provides methods of treating prophylactically an individual in whom Type 2 diabetes mellitus has not yet presented, but in whom there is an increased risk of developing such condition, which methods comprise administering to an individual in need thereof a pharmaceutical composition comprising effective amounts of a glycogen phosphorylase inhibitor and a non-glycogen phosphorylase inhibiting anti-diabetic agent; or effective amounts of a glycogen phosphorylase inhibitor and an anti-obesity agent.