341-92-4

Usage

Purification Methods

It crystallises from EtOH as yellow needles [Bunce et al. J Org Chem 52 4214 1987]. [Beilstein 5 III 1596, 5 IV 1675.]

InChI:InChI=1/C10H6FNO2/c11-9-5-6-10(12(13)14)8-4-2-1-3-7(8)9/h1-6H

Upstream product

• 321-38-0 1-Fluoronaphthalene 
• 776-34-1 1-amino-4-nitronaphthalene 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 573-03-5 4-fluoro-1-naphthoic acid 

Downstream Products

• 438-32-4 4-Fluoro-1-aminonaphthalene 
• 390-69-2 N-(4-fluoro-[1]naphthyl)-benzamide 
• 39139-76-9 1-(dimethylamino)-4-nitronaphthalene 
• 7000-88-6 N-methyl-4-nitro-α-naphthylamine 
• 326875-71-2 5-Benzyloxy-1-methoxy-4-(4-nitro-naphthalen-1-yloxy)-naphthalene 
• 326875-69-8 C₂₇H₁₉NO₄ 
• 1647-51-4 N-<4-Fluor-1-naphthyl>-N-nitroso-benzamid 
• 13772-59-3 3-bromo-1-fluoronaphthalene 
• 1229606-80-7 N-(4-(4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)pyridin-2-yl)-2-(2-methoxyacetamido)acetamide 
• 1229607-19-5 (R)-N-(4-(4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)pyridin-2-yl)-3-(dimethylamino)pyrrolidine-1-carboxamide 
• 1229607-55-9 2-amino-N-(4-(4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido)naphthalen-1-yloxy)pyridin-2-yl)acetamide 
• 1220627-13-3 di-tert-butyl 4-((4-(3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)ureido) naphthalen-1-yloxy)methyl)pyridin-3-yliminodicarbonate 
• 1220627-10-0 4-((4-nitronaphthalen-1-yloxy)methyl)pyridin-3-amine 
• 1220627-14-4 1-(4-((3-aminopyridin-4-yl)methoxy)naphthalen-1-yl)-3-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)urea 

Relevant academic research and scientific papers

Toll-like receptor-7 small molecule inhibitor and preparation method thereof

The invention belongs to the field of chemical small molecules, and particularly relates to a Toll-like receptor-7 small molecule inhibitor. The invention provides the Toll-like receptor-7 small molecule inhibitor, which takes a co-inhibitor of TLR7 and TLR8 obtained by screening as a research object, realizes selective regulation and control of TLR7 and TLR8 through the research on the structureoptimization and structure-activity relationship (SAR) of a parent compound, and further develops a high-efficiency, non-toxic and specific small molecule inhibitor with certain selectivity on TLR 7.The TLR7 small molecule inhibitor has a certain effect and potential medicinal value in autoimmune diseases (systemic lupus erythematosus).

Bismuth nitrate as a source of nitro radical in ipso-nitration of carboxylic acids

Aromatic nitro compounds are extensively used in synthetic chemistry. We disclose a new approach to obtain nitroarenes regioselectively starting from carboxylic acids under acid-free reaction conditions.

NH+ - F hydrogen bonding in a fluorinated "Proton Sponge" derivative: Integration of solution, solid-state, gas-phase, and computational studies

We report detailed studies on the characterization of an intramolecular NH - F hydrogen bond formed within a fluorinated "proton sponge" derivative. An ammonium ion, generated from 8-fluoro-N,N-dimethylnaphthalen-1- amine, serves as a charged hydrogen bond donor to a covalently bound fluorine appropriately positioned on the naphthalene skeleton. Potentiometric titrations of various N,N-dimethylnaphthalen-1-amines demonstrate a significant increase in basicity when hydrogen bonding is possible. X-ray crystallography reveals that NH - F hydrogen bonding in protonated 8-fluoro-N,N-di-methylnaphthalen-1-amine is heavily influenced by ion pairing in the solid state; bifurcated and trifurcated hydrogen bonds are formed depending on the counterion utilized. Compelling evidence of hydrogen bonding in the 8-fluoro-N,N-dimethylnaphthyl-1- ammonium cation is provided by gas-phase cryogenic vibrational photodissociation spectroscopy. Solution-phase infrared spectroscopy provides complementary results, and the frequencies of the N - H stretching mode in both phases are in excellent agreement with the computed vibrational spectra. NMR analysis of protonated 8-fluoro-N,N-dimethylnaphthalen-1-amine demonstrates significant H - F coupling between the N - H hydrogen and fluorine that cannot be attributed to long-range, through-bond interactions; the couplings correlate favorably with calculated values. The results obtained from these experiments are congruent with the formation of an NH - F hydrogen bond upon protonation of 8-fluoro-N,N-dimethylnaphthalen-1-amine.

FLUORINATED PHENYL-NAPHTHALENYL-UREA COMPOUNDS AS INHIBITORS OF CYTOKINES INVOLVED IN INFLAMMATORY PROCESSES

Disclosed are compounds of formula (I) wherein R1, R2, W and X of formula (I) are defined herein. The compounds inhibit production of cytokines involved in inflammatory processes and are thus useful for treating diseases and pathological conditions involving inflammation such as chronic inflammatory disease. Also disclosed are processes for preparing these compounds and pharmaceutical compositions comprising these compounds.

1,4-Disubstituted benzo-fused urea compounds

Disclosed are compounds of the formulas (I) and (II) shown below which are active as anti-inflammatory agents. Also disclosed are methods of using and making such compounds. wherein G, X, A and Q are described herein.