1692-79-1

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
N-[2-Nitro-4-(trifluoromethyl)phenyl]piperidine is utilized as a chemical entity in the discovery and development of new pharmaceuticals, targeting various medical conditions. Its unique structure may offer novel mechanisms of action or improved pharmacological properties compared to existing drugs.
Used in Organic Synthesis:
In the field of organic synthesis, N-[2-Nitro-4-(trifluoromethyl)phenyl]piperidine may serve as a key intermediate or building block for the synthesis of more complex organic molecules, including other pharmaceuticals, agrochemicals, or specialty chemicals.
Used in Chemical Manufacturing:
N-[2-NITRO-4-(TRIFLUOROMETHYL)PHENYL]PIPERIDINE may also find applications in chemical manufacturing processes, where its specific chemical properties could be leveraged to produce or modify other chemicals, contributing to the development of new materials or products.
Given the compound's potential applications and the ongoing research in its field, N-[2-Nitro-4-(trifluoromethyl)phenyl]piperidine is a subject of interest for further study and investigation to fully understand its capabilities and optimize its use in various industries.

InChI:InChI=1/C12H13F3N2O2/c13-12(14,15)9-4-5-10(11(8-9)17(18)19)16-6-2-1-3-7-16/h4-5,8H,1-3,6-7H2

Upstream product

• 121-17-5 2-chloro-3-nitro-5-trifluoromethylbenzene 
• 110-89-4 piperidine 
• 367-86-2 1-fluoro-2-nitro-4-trifluoromethyl-benzene 
• 1960-59-4 2-nitro-1-phenoxy-4-(trifluoromethyl)benzene 

Downstream Products

• 1496-40-8 2-(piperidin-1-yl)-5-(trifluoromethyl)benzenamine 
• 688033-18-3 3-iodo-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide 
• 926036-43-3 2-fluoro-5-iodo-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide 
• 926036-42-2 3-iodo-4-methyl-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide 
• 884602-75-9 5-(2-(2-aminopyrimidin-5-yl)ethynyl)-2-fluoro-N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)benzamide 
• 218156-96-8 SRPIN340 
• 865273-97-8 4-methoxy-3-(N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)sulfamoyl)benzoic acid 

Relevant academic research and scientific papers

Nucleophilic aromatic substitution reactions under aqueous, mild conditions using polymeric additive HPMC

The use of the inexpensive, benign, and sustainable polymer, hydroxypropyl methylcellulose (HPMC), in water enables nucleophilic aromatic subsitution (SNAr) reactions between various nucleophiles and electrophiles. The mild reaction conditions facilitate a broad functional group tolerance that can be utilized for subsequent derivatization for the synthesis of pharmaceutically relevant building blocks. The use of only equimolar amounts of all reagents and water as reaction solvent reveals the greenness and sustainability of the methodology presented herein.

Optimisation of 2-(N-phenyl carboxamide) triazolopyrimidine antimalarials with moderate to slow acting erythrocytic stage activity

Malaria is a devastating parasitic disease caused by parasites from the genus Plasmodium. Therapeutic resistance has been reported against all clinically available antimalarials, threatening our ability to control the disease and therefore there is an ongoing need for the development of novel antimalarials. Towards this goal, we identified the 2-(N-phenyl carboxamide) triazolopyrimidine class from a high throughput screen of the Janssen Jumpstarter library against the asexual stages of the P. falciparum parasite. Here we describe the structure activity relationship of the identified class and the optimisation of asexual stage activity while maintaining selectivity against the human HepG2 cell line. The most potent analogues from this study were shown to exhibit equipotent activity against P. falciparum multidrug resistant strains and P. knowlesi asexual parasites. Asexual stage phenotyping studies determined the triazolopyrimidine class arrests parasites at the trophozoite stage, but it is likely these parasites are still metabolically active until the second asexual cycle, and thus have a moderate to slow onset of action. Non-NADPH dependent degradation of the central carboxamide and low aqueous solubility was observed in in vitro ADME profiling. A significant challenge remains to correct these liabilities for further advancement of the 2-(N-phenyl carboxamide) triazolopyrimidine scaffold as a potential moderate to slow acting partner in a curative or prophylactic antimalarial treatment.

Discovery of Selective Inhibitors of Endoplasmic Reticulum Aminopeptidase 1

ERAP1 is an endoplasmic reticulum-resident zinc aminopeptidase that plays an important role in the immune system by trimming peptides for loading onto major histocompatibility complex proteins. Here, we report discovery of the first inhibitors selective for ERAP1 over its paralogues ERAP2 and IRAP. Compound 1 (N-(N-(2-(1H-indol-3-yl)ethyl)carbamimidoyl)-2,5-difluorobenzenesulfonamide) and compound 2 (1-(1-(4-acetylpiperazine-1-carbonyl)cyclohexyl)-3-(p-tolyl)urea) are competitive inhibitors of ERAP1 aminopeptidase activity. Compound 3 (4-methoxy-3-(N-(2-(piperidin-1-yl)-5-(trifluoromethyl)phenyl)sulfamoyl)benzoic acid) allosterically activates ERAP1's hydrolysis of fluorogenic and chromogenic amino acid substrates but competitively inhibits its activity toward a nonamer peptide representative of physiological substrates. Compounds 2 and 3 inhibit antigen presentation in a cellular assay. Compound 3 displays higher potency for an ERAP1 variant associated with increased risk of autoimmune disease. These inhibitors provide mechanistic insights into the determinants of specificity for ERAP1, ERAP2, and IRAP and offer a new therapeutic approach of specifically inhibiting ERAP1 activity in vivo.

Trifluoromethyl arylamides with antileukemia effect and intracellular inhibitory activity over serine/arginine-rich protein kinases (SRPKs)

The serine/arginine-rich protein kinases (SRPKs) have frequently been found with altered activity in a number of cancers, suggesting they could serve as potential therapeutic targets in oncology. Here we describe the synthesis of a series of twenty-two tr

The effects of ring substituents and leaving groups on the kinetics of SNAr reactions of 1-halogeno- and 1-phenoxy-nitrobenzenes with aliphatic amines in acetonitrile

Rate constants are reported for the reactions of a series of 1-chloro-, 1-fluoro- and 1-phenoxy-nitrobenzenes activated by CF3 or CN groups or by ring-nitrogen with n-butylamine, pyrrolidine or piperidine in acetonitrile. The results are compar

A cavitand stabilizes the Meisenheimer complex of SNAr reactions

A deep cavitand binds amine nucleophiles and accelerates their subsequent SNAr reactions by solvating the intermediate Meisenheimer complex. The Royal Society of Chemistry.

Alkynylpyrimidine amide derivatives as potent, selective, and orally active inhibitors of Tie-2 kinase

The recognition that aberrant angiogenesis contributes to the pathology of inflammatory diseases, cancer, and myocardial ischemia has generated considerable interest in the molecular mechanisms that regulate blood vessel growth. The receptor tyrosine kinase Tie-2 is expressed primarily by vascular endothelial cells and is critical for embryonic vasculogenesis. Interference with the Tie-2 pathway by diverse blocking agents such as soluble Tie-2 receptors, anti-Tie-2 intrabodies, anti-Ang-2 antibodies, and peptide-F c conjugates has been shown to suppress tumor growth in xenograft studies. An alternative strategy for interfering with the Tie-2 signaling pathway involves direct inhibition of the kinase functions of the Tie-2 receptor. Herein we describe the development of alkynylpyrimidine amide derivatives as potent, selective, and orally available ATP-competitive inhibitors of Tie-2 autophosphorylation.

METHOD OF REGULATING PHOSPHORYLATION OF SR PROTEIN AND ANTIVIRAL AGENTS COMPRISING SR PROTEIN ACTIVITY REGULATOR AS THE ACTIVE INGREDIENT

The present invention provides: (1) antiviral agents that act by reducing or inhibiting the activity of SR proteins, more specifically, (i) antiviral agents that act by enhancing dephosphorylation of SR proteins, and (ii) antiviral agents that act by inhi

Methine dyes

The invention relates to a new class of pyrrolobenzimidazole, benzimidazoloisoquinoline and dipyrodinobenzodiimidazole in cyanine sensitizing dyes derived therefrom and their use in silver halide emulsions, and to methods for preparation of such new dyes.