17040-20-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Anilinobenzoic acid is used as a building block for the synthesis of various pharmaceuticals and dyes. It plays a crucial role in the production of sunscreen and local anesthetic preparations due to its UV-absorbing properties.
Used in Cosmetics Industry:
In the cosmetics industry, 4-Anilinobenzoic acid is used as an ingredient in hair dyes and pigments, capitalizing on its ability to absorb UV radiation and provide coloration.
Used in Research and Development:
4-Anilinobenzoic acid is also utilized in research for its potential application in the treatment of various medical conditions, such as depression and neuropathic pain, highlighting its versatility and importance in the development of new therapeutic agents.

InChI:InChI=1/C13H11NO2/c15-13(16)10-6-8-12(9-7-10)14-11-4-2-1-3-5-11/h1-9,14H,(H,15,16)

Upstream product

• 62-53-3 aniline 
• 64678-66-6 ethyl 4-(phenylamino)benzoate 
• 94-09-7 p-aminoethylbenzoate 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 150-13-0 4-amino-benzoic acid 
• 586-76-5 4-Bromobenzoic acid 
• 98-80-6 phenylboronic acid 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 108-90-7 chlorobenzene 
• 536-90-3 m-Anisidine 
• 12775-96-1 copper 
• 96-99-1 4-chloro-3-nitrobenzoate 
• 53451-85-7 N-phenyl-4-trifluoromethylacetanilide 
• 349-97-3 4-(trifluromethyl)acetanilide 

Downstream Products

• 4058-18-8 methyl 4-(phenylamino)benzoate 
• 1377997-17-5 C₂₂H₂₉N₃O 
• 1382992-66-6 N-(2-(5-chloro-1H-indol-3-yl)ethyl)-4-(phenylamino)benzamide 
• 143667-39-4 4-anilino-benzoic acid hydrazide 
• 64678-66-6 ethyl 4-(phenylamino)benzoate 

Relevant academic research and scientific papers

SEROTONIN 5-HT2B INHIBITORY COMPOUNDS

The compounds of the invention, as described herein, are novel serotonin 5-HT2B antagonists useful for the treatment of myxomatous mitral valve degeneration (MMVD), congestive heart failure (CHF), and/or asymptomatic heart failure in animals, preferably c

The synthesis of a [2.2]paracyclophane-derived secondary phosphine oxide and a study of its reactivity

A planar chiral secondary phosphine oxide based on [2.2]paracyclophane was synthesized and its chemistry investigated; it was shown to be a competent pre-ligand in palladium(0)-mediated reactions, and displayed promising activity in gold(I)-catalysed cyclisations. The secondary phosphine oxide could be transformed into a collection of P-stereogenic tertiary phosphine oxides. These are rare examples of the planar chirality of [2.2]paracyclophane being combined with a P-stereogenic centre. Unfortunately, epimerisation of the phosphorus stereocentre during reduction limits the use of this chemistry.

Palladium-catalyzed amination of aryl sulfoxides

Amination of diaryl sulfoxides with anilines and alkylamines has been accomplished under palladium/N-heterocyclic carbene (NHC) catalysis. Owing to its electron deficiency, the leaving arenesulfenate anion would be smoothly released from the palladium center to result in uneventful catalyst turnover under milder reaction conditions in comparison with previous C-S bond amination reactions. This amination accommodated a wider range of functional groups such as silyl, boryl, methylsulfanyl, and halogen moieties. Regioselective amination of unsymmetrical diaryl sulfoxides was also executed by means of steric bias.

Pd/AlO(OH): A Heterogeneous, Stable and Recyclable Catalyst for N-Arylation of Aniline Under Ligand-Free Aerobic Condition

Abstract: Many synthetic methods have been reported to construct an aryl-nitrogen bond. But they mainly suffer from the usage of expensive ligands. Herein, we report highly effective, heterogeneous, reusable and ligand-free nanocatalyst for the Buchwald-Hartwig coupling reaction under aerobic condition. Wafer-like structure with nano-porous nature of AlO(OH) was identified with TEM and BET surface area analyses. Zero valent Pd nanoparticles (with less than 10?nm crystallite size which strongly evident from TEM analysis) were observed in XRD pattern, which was further confirmed by XPS studies. The reaction conditions were optimized and the scope of the reaction was extended with various aryl halides and aniline using low amount of Pd (0.31?mol%) based heterogeneous catalyst. Heterogeneity, reusability and stability (confirmed by XRD) were found to be reasonable. Use of meagre amount of Pd and the ligand-free aerobic condition make this system economically as well as environmentally feasible. Graphical Abstract: [Figure not available: see fulltext.].

Bifunctional AKR1C3 inhibitors/androgen receptor modulators and methods of use thereof

The invention includes compositions comprising selective AKR1C3 inhibitors. The invention also includes compositions comprising bifunctional AKR1C3 inhibitors and selective androgen receptor modulators. The invention further includes methods of treatment using the compositions of the invention.

Evaluation of Novel N-(piperidine-4-yl)benzamide Derivatives as Potential Cell Cycle Inhibitors in HepG2 Cells

In this study, a series of novel N-(piperidine-4-yl)benzamide derivatives was designed, synthesized, and evaluated for antitumor activity. Some compounds were found to have potent antitumor activity. In particular, compound 47 showed the most potent biological activity against HepG2 cells, with an IC50 value of 0.25 μm. Western blot analysis demonstrated that compound 47 inhibited the expression of cyclin B1 and p-Rb and enhanced the expression of p21, p53, Rb, and phospho-adenosine monophosphate-activated protein kinase (p-AMPK). Further, cell cycle arrest was observed by flow cytometry (FCM). In summary, compound 47 was screened to have potential activity for the treatment of hepatocarcinoma via the induction of cell cycle arrest by a p53/p21-dependent pathway.

Unique copper-salen complex: An efficient catalyst for N-arylations of anilines and imidazoles at room temperature

We have reported here the catalytic activity of a unique Cu-salen type complex in N-arylation of anilines with arylboronic acids in water. The protocol is found to be applicable for a wide range of electronically diversified arylboronic acids and anilines with excellent yields of the isolated product. Further the scope of this protocol has been extended to the synthesis of various N-aryl imidazoles in iso-propanol.

NEW COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

This invention provides novel compounds and the novel compounds for use as a medicine, more in particular for the prevention or treatment of neurodegenerative disorders, more specifically certain neurological disorders, such as disorders collectively known as tauopathies, and disorders characterised by cytotoxic α-synuclein amyloidogenesis. The present invention also relates to the use of said novel compounds for the manufacture of medicaments useful for treating such neurodegenerative disorders. The present invention further relates to pharmaceutical compositions including said novel compounds and to methods for the preparation of said novel compounds. The compounds have the formula (A1) wherein R1, R2, R4, R6, E, n, Y1, Y2, Y3, Y4, Y5, L, B, R8, and m are as defined in the claims.

Development of potent and selective inhibitors of aldo-keto reductase 1C3 (type 5 17β-hydroxysteroid dehydrogenase) based on N -phenyl-aminobenzoates and their structure-activity relationships

Aldo-keto reductase 1C3 (AKR1C3; type 5 17β-hydroxysteroid dehydrogenase) is overexpressed in castration resistant prostate cancer (CRPC) and is implicated in the intratumoral biosynthesis of testosterone and 5α-dihydrotestosterone. Selective AKR1C3 inhibitors are required because compounds should not inhibit the highly related AKR1C1 and AKR1C2 isoforms which are involved in the inactivation of 5α-dihydrotestosterone. NSAIDs, N-phenylanthranilates in particular, are potent but nonselective AKR1C3 inhibitors. Using flufenamic acid, 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid, as lead compound, five classes of structural analogues were synthesized and evaluated for AKR1C3 inhibitory potency and selectivity. Structure-activity relationship (SAR) studies revealed that a meta-carboxylic acid group relative to the amine conferred pronounced AKR1C3 selectivity without loss of potency, while electron withdrawing groups on the phenylamino B-ring were optimal for AKR1C3 inhibition. Lead compounds did not inhibit COX-1 or COX-2 but blocked the AKR1C3 mediated production of testosterone in LNCaP-AKR1C3 cells. These compounds offer promising leads toward new therapeutics for CRPC.

NEW COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES

This invention provides novel compounds and the novel compounds for use as a medicine, more in particular for the prevention or treatment of neurodegenerative disorders, more specifically certain neurological disorders, such as disorders collectively known as tauopathies, and disorders characterised by cytotoxic α-synuclein amyloidogenesis. The present invention also relates to the use of said novel compounds for the manufacture of medicaments useful for treating such neurodegenerative disorders. The present invention further relates to pharmaceutical compositions including said novel compounds and to methods for the preparation of said novel compounds. The compounds have the formula (A1) wherein R1, R2, R4, R6, E, n, Y1, Y2, Y3, Y4, Y5, L, B, R8, and m are as defined in the claims.