131885-34-2

Basic information

• Product Name: N-Benzyl-5-fluoro-2-nitroaniline
• Synonyms: N-Benzyl-5-fluoro-2-nitroaniline
• CAS NO: 131885-34-2
• Molecular Formula: C₁₃H₁₁FN₂O₂
• Molecular Weight: 246.2370432
• Mol File: 131885-34-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 386.4±37.0 °C(Predicted)
• Appearance: /
• Density: 1.326±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -1.30±0.10(Predicted)
• CAS DataBase Reference: N-Benzyl-5-fluoro-2-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-Benzyl-5-fluoro-2-nitroaniline(131885-34-2)
• EPA Substance Registry System: N-Benzyl-5-fluoro-2-nitroaniline(131885-34-2)

Safety Data

• Hazardous Substances Data: 131885-34-2(Hazardous Substances Data)

Upstream product

• 700-36-7 2-bromo-4-fluoronitrobenzene 
• 100-46-9 benzylamine 
• 446-35-5 2,4-Difluoronitrobenzene 

Downstream Products

• 951666-39-0 methyl 5-(3-benzylamino-4-nitro-phenoxy)-2-(toluene-4-sulfonylamino)-benzoate 
• 346704-07-2 benzyl-(2-nitro-5-piperazin-1-yl-phenyl)-amine 
• 1250244-09-7 N¹-benzyl-5-fluorobenzene-1,2-diamine 

Relevant articles and documents

Discovery of 5-(4-methylpiperazin-1-yl)-2-nitroaniline derivatives as a new class of SIRT6 inhibitors

SIRT6 is a deacetylase of histone H3 and inhibitors of SIRT6 have been thought as potential agents for treatment of diabetes. Herein we report the discovery of a series of new SIRT6 inhibitors containing the skeleton 1-phenylpiperazine. Among them, compound 5-(4-methylpiperazin-1-yl)-2-nitroaniline (6d) is the most potent one, which showed an IC50 value of 4.93 μM against SIRT6 in the Fluor de Lys (FDL) assay. It displayed KD values of 9.76 μM and 10 μM in surface plasmon resonance (SPR) and isothermal titration calorimetry (ITC) assays, respectively. In selectivity assay, 6d showed no activity against other members of the HDAC family (SIRT1-3 and HDAC1-11) at concentrations up to 200 μM. In a mouse model of type 2 diabetes, 6d could significantly increase the level of glucose transporter GLUT-1, thereby reducing blood glucose. Overall, this study provides a promising lead compound for subsequent drug discovery targeting SIRT6.

Discovery and Characterization of 2-Nitro-5-(4-(phenylsulfonyl)piperazin-1-yl)- N-(pyridin-4-ylmethyl)anilines as Novel Inhibitors of the Aedes aegypti Kir1 (AeKir1) Channel

Mosquito-borne arboviral diseases such as Zika, dengue fever, and chikungunya are transmitted to humans by infected adult female Aedes aegypti mosquitoes and affect a large portion of the world's population. The Kir1 channel in Ae. aegypti (AeKir1) is an important ion channel in the functioning of mosquito Malpighian (renal) tubules and one that can be manipulated in order to disrupt excretory functions in mosquitoes. We have previously reported the discovery of various scaffolds that are active against the AeKir1 channel. Herein we report the synthesis and biological characterization of a new 2-nitro-5-(4-(phenylsulfonyl) piperazin-1-yl)-N-(pyridin-4-ylmethyl)anilines scaffold as inhibitors of AeKir1. This new scaffold is more potent in vitro compared to the previously reported scaffolds, and the molecules kill mosquito larvae.

PYRIDINONES

The present invention encompasses compounds of general formula (I) wherein the groups R1 to R3 and X1 through X6 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.