55751-56-9

Usage

General Description

2-(2-isopropyl-phenylamino)-benzoic acid, also known as fenoprofen, is a nonsteroidal anti-inflammatory drug (NSAID) that is used to reduce pain, inflammation, and fever. It works by inhibiting the production of prostaglandins, which are responsible for causing pain and inflammation in the body. Fenoprofen is often prescribed for conditions such as rheumatoid arthritis, osteoarthritis, and menstrual pain. It is usually taken in the form of tablets or capsules, and its effects can last for up to 8 hours. Like other NSAIDs, fenoprofen may have potential side effects such as stomach irritation, bleeding, and increased risk of heart attack or stroke, especially with long-term use. It is important to use this medication as prescribed by a healthcare professional and to follow their advice about potential risks and benefits.

InChI:InChI=1/C16H17NO2/c1-11(2)12-7-3-5-9-14(12)17-15-10-6-4-8-13(15)16(18)19/h3-11,17H,1-2H3,(H,18,19)

Upstream product

• 1488-42-2 Diphenyliodonium-2-carboxylate 
• 643-28-7 2-isopropylaniline 
• 118-91-2 ortho-chlorobenzoic acid 
• 88-65-3 2-bromobenzoic-acid 

Relevant academic research and scientific papers

Chiral 1,8-Diarylnaphthalenes, Methods of Making Them, and Their Use as Sensors

One aspect of the invention relates to 1,8-diarylnaphthalene compounds. In certain embodiments, a compound of the invention is an N-oxide of a 1,8-diarylnaphthalene. In certain embodiments, the aryl group is an optionally substituted acridyl group. In certain embodiments, a compound of the invention is a single steroisomer. In certain embodiments, a compound of the invention is a single enantiomer. Another aspect of the present invention relates to a method of detecting the presence of an analyte in a sample by monitoring the fluorescence of a compound of the invention in a sample. In certain embodiments, the analyte is a metal ion. Another aspect of the present invention relates to a method of determining the enantiomeric purity of an analyte by monitoring the fluorescence of a compound of the invention in the presence of the analyte. In certain embodiments, the analyte is a compound that is capable of hydrogen bonding.

Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines

A chemo- and regioselective copper-catalyzed cross-coupling procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection and produces N-aryl and N-alkyl anthranilic acid derivatives in up to 99% yield. N-(1-Pyrene)anthranilic acid has been employed in metal ion-selective fluorosensing. Titration experiments showed that this pyrene-derived amino acid forms an equimolar complex with Hg(II) in water resulting in selective fluorescence quenching even in the presence of other metal ions such as Zn(II) and Cd(II).

Regioselective copper-catalyzed amination of chlorobenzoic acids: Synthesis and solid-state structures of N-aryl anthranilic acid derivatives

A chemo- and regioselective copper-catalyzed cross-coupling reaction for effective amination of 2-chlorobenzoic acids with aniline derivatives has been developed. The method eliminates the need for acid protection and produces a wide range of N-aryl anthranilic acid derivatives in up to 99% yield. The amination was found to proceed with both electron-rich and electron-deficient aryl chlorides and anilines and also utilizes sterically hindered anilines such as 2,6-dimethylaniline and 2-tert-butylaniline. The conformational isomerism of appropriately substituted N-aryl anthranilic acids has been investigated in the solid state. Crystallographic analysis of seven anthranilic acid derivatives showed formation of two distinct supramolecular architectures exhibiting trans-anti and unprecedented trans-syn dimeric structures.

Synthesis of conformationally stable 1,8-diarylnaphthalenes: Development of new photoluminescent sensors for ion-selective recognition

Highly constrained 1,8-diarylnaphthalenes exhibiting stability to isomerization have been prepared utilizing two consecutive CuO-promoted Stille cross-couplings of 1,8-dibromonaphthalene and 4-alkyl-9-trimethylstannylacridines, Screening of Pd catalysts Pd(PPh 3)4, PdCl2dppf, or Pd2(dba) 3/t-Bu3P and bases such as Cy2NMe, t-BuOK, K3PO4, and Cs2CO3 in DME or DMF revealed superior results of Stille over Suzuki coupling with acridylboronic acids or pinacolate derivatives. The meso syn- and C2-symmetric antiisomers of 1,8-bis(4,4′-dimethyl-9,9′-diacridyl)naphthalene, 2, and 1,8-bis(4,4′-diisopropyl-9,9′-diacridyl)-naphthalene, 3, did not show any sign of syn/anti-interconversion after heating to 180 °C for 24 h, Using the Eyring equation, we calculated the Gibbs standard activation energy for isomerization, ΔGo?, to be higher than 180 kJ/mol. PM3 calculations of 2 and 3 suggest a highly congested structure exhibiting two parallel acridyl moieties perpendicular to the naphthalene ring. UV and fluorescence spectroscopy studies of 2 and 3 revealed remarkable quantum yields of these blue and green light emitters, Fluorescence titration experiments with the syn-isomer of 2 showed highly efficient quenching by Cu(II) ions, whereas almost no quenching effects were observed with Cu(I) and Zn(II) salts. The striking difference in fluorescence quenching was attributed to significant photoinduced electron transfer, resulting in nonradiative relaxation of excited Cu(II)-syn-2, Stern-Voelmer plots of syn-2 in the presence of CuCl2 showed a sigmoidal quenching curve indicating cooperative recognition, whereas a linear response was observed with CuCl and ZnCl2, Fluorescence experiments in the presence of various amounts of CuCl, CuBr, and Cu(ACN)4BF4 proved that the quenching is cation selective and independent of the nature of counteranions.

Discovery and structure-activity relationship of oxalylarylaminobenzoic acids as inhibitors of protein tyrosine phosphatase 1B

Protein Tyrosine phosphatase 1B (PTP1B) has been implicated as a key negative regulator of both insulin and leptin signaling pathways. Using an NMR-based screening approach with 15N- and 13C-labeled PTP1B, we have identified 2,3-dimethylphenyloxalylaminobenzoic acid (1) as a general, reversible, and competitive PTPase inhibitor. Structure-based approach guided by X-ray crystallography facilitated the development of 1 into a novel series of potent and selective PTP1B inhibitors occupying both the catalytic site and a portion of the noncatalytic, second phosphotyrosine binding site. Interestingly, oral biovailability has been observed in rats for some compounds. Furthermore, we demonstrated in vivo plasma glucose lowering effects with compound 12d in ob/ob mice.