315239-67-9

Usage

Chemical class

Piperazine derivatives

Explanation

1-METHYL-4-[2-NITRO-4-(TRIFLUOROMETHYL)PHENYL]PIPERAZINE is a compound that belongs to the class of piperazine derivatives.

Explanation

This piperazine derivative has a specific structure that includes a trifluoromethyl-nitro-phenyl-substituted-phenyl group.

Explanation

The molecular formula of 1-METHYL-4-[2-NITRO-4-(TRIFLUOROMETHYL)PHENYL]PIPERAZINE is C13H15F3N4O2, indicating the number of carbon, hydrogen, fluorine, nitrogen, and oxygen atoms in the compound.

Explanation

The compound is used in the field of medicinal chemistry and pharmaceuticals due to its potential pharmacological properties.

Explanation

1-METHYL-4-[2-NITRO-4-(TRIFLUOROMETHYL)PHENYL]PIPERAZINE may have potential toxic effects, so it is important to handle this chemical compound with caution. It should only be handled by trained professionals in a controlled laboratory setting to ensure safety.

Structural features

Trifluoromethyl-nitro-phenyl-substituted-phenyl group

Application

Medicinal chemistry and pharmaceuticals

Precautions

Potential toxic effects, handling by trained professionals, controlled laboratory setting

Upstream product

• 109-01-3 1-methyl-piperazine 
• 367-86-2 1-fluoro-2-nitro-4-trifluoromethyl-benzene 

Downstream Products

• 926036-45-5 N-(2-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl)-2-fluoro-5-iodobenzamide 
• 685853-98-9 2-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)aniline 

Relevant academic research and scientific papers

Novel pyrazole amide compound and preparation thereof, and application of novel pyrazole amide compound in prevention and treatment of plant pathogenic diseases and pest killing

The invention relates to a novel pyrazole amide compound I and a preparation method thereof and application of the novel pyrazole amide compound I in prevention and treatment of plant pathogenic disease and pest killing. The novel pyrazole amide compound

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.

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.

PROTEIN KINASE MODULATORS AND METHOD OF USE

The present invention relates to chemical compounds having a general formula I wherein A, B, D, E, G, H1-5 and R1-4 are defined herein, and synthetic intermediates, which are capable of modulating various protein kinase receptor enzymes and, thereby, influencing various disease states and conditions related to the activities of these kinases. For example, the compounds are capable of modulating kinase enzymes thereby influencing the process of angiogenesis and treating angiogenesis-related diseases and other poliferative disorders, including cancer and inflammation. The invention also includes pharmaceutical compositions, including the compounds, and methods of treating disease states related to the activity of protein kinases.