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Usage

Uses

Used in Pharmaceutical Industry:
4-amino-N-(2-phenylethyl)benzamide is used as a potential analgesic for the management of pain. Its unique structure may contribute to its efficacy in alleviating pain, making it a promising candidate for further research and development in pain management.
Used in Neurological Applications:
4-amino-N-(2-phenylethyl)benzamide is used as a potential anticonvulsant for the treatment of seizure disorders. Its ability to modulate neuronal activity and reduce seizure frequency could make it a valuable addition to the arsenal of antiepileptic drugs.
Used in Medicinal Chemistry:
4-amino-N-(2-phenylethyl)benzamide is used as a building block for the synthesis of novel organic compounds. Its unique structure and potential pharmaceutical properties make it a valuable component in the development of new drugs and therapeutic agents.

InChI:InChI=1/C15H16N2O/c16-14-8-6-13(7-9-14)15(18)17-11-10-12-4-2-1-3-5-12/h1-9H,10-11,16H2,(H,17,18)

Upstream product

• 150-13-0 4-amino-benzoic acid 
• 64-04-0 phenethylamine 
• 122-04-3 4-nitro-benzoyl chloride 
• 66493-39-8 4-(N-tert-butoxycarbonyl)aminobenzoic acid 
• 327037-49-0 4-[(tert-butoxycarbonyl)amino]-N-(β-phenethyl)benzamide 
• 62497-65-8 4-nitro-N-phenethylbenzamide 
• 62-23-7 4-nitro-benzoic acid 

Downstream Products

• 947488-98-4 1,1'-bis[N-phenethylbenzamidoimine]ferrocene 
• 108191-14-6 4-Dimethylamino-N-phenethyl-benzamide 
• 1372892-88-0 C₂₅H₁₉ClN₂O₃ 

Relevant academic research and scientific papers

Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HTS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial β-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure-activity relationships of these compounds were explored.

Comparative study of dG affinity vs. DNA methylation modulating properties of side chain derivatives of procainamide: Insight into its DNA hypomethylating effect

Procainamide derivatives have been synthesized to investigate the role of side chains in modulating the DNA methylation level in cancer cells and gain insight into its mechanism of action. The synthesized derivatives comprised of flexible (dimethyl), cons

Aryl amide small-molecule inhibitors of microRNA miR-21 function

MicroRNAs (miRNAs) are single stranded RNA molecules of ～22 nucleotides that negatively regulate gene expression. MiRNAs are involved in fundamental cellular processes, such as development, differentiation, proliferation, and survival. MiRNA misregulation has been linked to various human diseases, most notably cancer. MicroRNA-21 (miR-21), a well-established oncomiR, is significantly overexpressed in many types of human cancers, thus rendering miR-21 a potential therapeutic target. Using a luciferase-based reporter assay under the control of miR-21 expression, a high-throughput screen of >300,000 compounds led to the discovery of a new aryl amide class of small-molecule miR-21 inhibitors. Structure-activity relationship (SAR) studies resulted in the development of four aryl amide derivatives as potent and selective miR-21 inhibitors. The intracellular levels of various miRNAs in HeLa cells were analyzed by qRT-PCR revealing specificity for miR-21 inhibition over other miRNAs. Additionally, preliminary mechanism of action studies propose a different mode of action compared to previously reported miR-21 inhibitors, thus affording a new chemical probe for future studies.

Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1

Arginine methylation is an epigenetic modification that receives increasing interest as it plays an important role in several diseases. This is especially true for hormone-dependent cancer, seeing that histone methylation by arginine methyltransferase I (PRMT1) is involved in the activation of sexual hormone receptors. Therefore, PRMT inhibitors are potential drugs and interesting tools for cell biology. A dapsone derivative called allantodapsone previously identified by our group served as a lead structure for inhibitor synthesis. Acylated derivatives of p-aminobenzenesulfonamides and the antilepra drug dapsone were identified as new inhibitors of PRMT1 by in vitro testing. The bis-chloroacetyl amide of dapsone selectively inhibited human PRMT1 in the low micromolar region and was selective for PRMT1 as compared to the arginine methyltransferase CARM1 and the lysine methyltransferase Set7/9. It showed anticancer activity on MCF7a and LNCaP cells and blocked androgen dependent transcription specifically in a reporter gene system. Likewise, a transcriptional block was also demonstrated in LNCaP cells using quantitative RT-PCR on the mRNA of androgen dependent genes.

Synthesis and physico-analytical studies of some novel ferrocenyl Schiff base derivatives

A series of ferrocenyl Schiff base derivatives was synthesized by condensation reactions of 1,1′-ferrocenedicarboxaldehyde and aromatic amines containing long chain alkyl groups as free ends which were characterized by their physical properties, elemental

Design, synthesis, and biological evaluation of a series of lavendustin A analogues that inhibit EGFR and Syk tyrosine kinases, as well as tubulin polymerization

A series of N-alkylamide analogues of the lavendustin A pharmacophore were synthesized and tested for inhibitiofi of the epidermal growth factor receptor (EGFR) protein tyrosine kinase and the nonreceptor protein tyrosine kinase Syk. Although several comp

Anticonvulsant activity of some 4-aminobenzamides

A series of 4-aminobenzamides of some simple primary and secondary amines were prepared and evaluated for anticonvulsant effects. The compounds were tested in mice against seizures induced by electroshock and pentylenetetrazole (metrazole) and in the rotorod assay for neurologic deficit. For those N-alkyl amides tested, 4-amino-N-amylbenzamide was the most potent against maximal electroshock seizures (MES): ED50=42.98 mg/kg; however, the N-cyclohexylbenzamide showed the greatest protective index (PI=TD50/ED50), 2.8. The introduction of a second aromatic ring produced more potent compounds, with d,l-4-amino-N-(α-methylbenzyl)-benzamide showing the highest level of activity. This compound has an anti-MES ED50 of 18.02 mg/kg in mice when administered intraperitoneally (ip) and a TD50 of 170.78 mg/kg (PI=9.5) in the same species. These data compare quite favorably with those for phenobarbital and phenytoin in the same assays.