23975-58-8

Usage

Uses

Used in Ophthalmology:
1-(3-Fluorophenyl)-4,4,4-trifluorobutane-1,3-dione is used as an antiviral medication for the treatment of eye infections caused by the herpes simplex virus. It is particularly effective in reducing the symptoms and duration of viral eye infections, such as conjunctivitis and keratitis. The antiviral action of trifluridine helps to control the viral load, alleviate inflammation, and promote healing of the affected ocular tissues.
However, it is important to note that trifluridine may cause some side effects, such as eye irritation, stinging, and blurred vision. These side effects are generally mild and transient, but patients should be advised to report any persistent or severe symptoms to their healthcare provider.

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 455-36-7 1-(3-fluorophenyl)ethanone 

Downstream Products

• 1581726-13-7 C₁₉H₁₅F₄N₃O₂S 
• 1271477-23-6 C₁₃H₆F₄N₂O 
• 1271475-19-4 C₁₃H₆F₄N₂S 

Relevant academic research and scientific papers

An SAR study of hydroxy-trifluoromethylpyrazolines as inhibitors of Orai1-mediated store operated Ca2+ entry in MDA-MB-231 breast cancer cells using a convenient Fluorescence Imaging Plate Reader assay

The proteins Orai1 and STIM1 control store-operated Ca2+ entry (SOCE) into cells. SOCE is important for migration, invasion and metastasis of MDA-MB-231 human triple negative breast cancer (TNBC) cells and has been proposed as a target for cancer drug discovery. Two hit compounds from a medium throughput screen, displayed encouraging inhibition of SOCE in MDA-MB-231 cells, as measured by a Fluorescence Imaging Plate Reader (FLIPR) Ca2+ assay. Following NMR spectroscopic analysis of these hits and reassignment of their structures as 5-hydroxy-5-trifluoromethylpyrazolines, a series of analogues was prepared via thermal condensation reactions between substituted acylhydrazones and trifluoromethyl 1,3-dicarbonyl arenes. Structure-activity relationship (SAR) studies showed that small lipophilic substituents at the 2- and 3-positions of the RHS and 2-, 3- and 4-postions of the LHS terminal benzene rings improved activity, resulting in a novel class of potent and selective inhibitors of SOCE.

Discovery and structure-activity relationships study of novel thieno[2,3-b]pyridine analogues as hepatitis C virus inhibitors

Current treatment for hepatitis C is barely satisfactory, there is an urgent need to develop novel agents for combating hepatitis C virus infection. This study discovered a new class of thieno[2,3-b]pyridine derivatives as HCV inhibitors. First, a hit compound characterized by a thienopyridine core was identified in a cell-based screening of our privileged small molecule library. And then, structure activity relationship study of the hit compound led to the discovery of several potent compounds without obvious cytotoxicity in vitro (12c, EC50 = 3.3 μM, SI >30.3, 12b, EC50 = 3.5 μM, SI >28.6, 10l, EC50 = 3.9 μM, SI >25.6, 12o, EC 50 = 4.5 μM, SI >22.2, respectively). Although the mechanism of them had not been clearly elucidated, our preliminary optimization of this class of compounds had provided us a start point to develop new anti-HCV agents.

Synthesis and characterization of the titanium complexes bearing two β-enaminoketonato ligands with electron withdrawing groups/modified phenyls and their behaviors for ethylene (co-)polymerization

A series of new titanium complexes with two asymmetric bidentate β-enaminoketonato [N,O] ligands (2b-t), [PhNC(CF3)CHC(Ar)O] 2TiCl2 (2b, Ar = -C6H4F(o); 2c, Ar = -C6H4F(m); 2d, Ar = -C6H4F(p); 2e, Ar = -C6H4Cl(p); 2f, Ar = -C6H 4OMe(p); 2g, Ar = -C6H4CF3(p); 2h, Ar = -C6H4CF3(m); 2i, Ar = -C6H 4CF3(o); 2j, Ar = -C6H4Cl(o); 2k, Ar = -C6H4Br(o); 2l, Ar = -C6H4I(o); 2m, Ar = -C6H3F2(2,4); 2n, Ar = -C 6H3F2(2,6); 2o, Ar = -C6H 3F2(3,4); 2p, Ar = -C6H3F 2(3,5); 2q, Ar = -C6F5; 2r, Ar = C 6F4OMe; 2s, Ar = -C6H3Cl 2(2,6); 2t, Ar = -C6H3Cl2(2,5)), have been synthesized based on substituted acetophenones. X-Ray analyses reveal that complexes 2h, 2k, 2m, and 2n adopt distorted octahedral geometry around the titanium center, in which the two chloride ligands are situated in the cis-orientation. 2s also adopts distorted octahedral geometry, but the two chloride ligands in it are situated in the trans-orientation due to the increase of the steric effect of the phenyl derived from the acetophenone. The influence of the substituent effects on catalyst performance, including catalytic activities and the molecular weight distribution of the polymers obtained, was investigated in detail. With modified methylaluminoxane (MMAO) as a cocatalyst, complexes 2b-r and 2t are active catalysts for ethylene polymerization at room temperature, and produce high molecular weight polymers. It is observed that the catalytic activities are significantly enhanced by introducing some electron-withdrawing groups, such as -F, -Cl and -CF3, into the suitable positions of the phenyl ring close to the oxygen donor. It should be noted that complexes 2c-i, 2p, 2n and 2t are also capable of promoting the living copolymerization of ethylene with norbornene at room temperature, yielding high molecular weight copolymers with narrow molecular weight distributions (PDI = 1.05-1.30). The Royal Society of Chemistry 2010.

ISOXAZOLE-IMIDAZOLE DERIVATIVES

The present invention is concerned isoxazole-imidazole derivatives having affinity and selectivity for GABA A α5 receptor binding site, their manufacture, pharmaceutical compositions containing them and their use for enhancing cognition or for the treatment of cognitive disorders like Alzheimer's disease. In particular, the present invention is concerned with aryl-isoxazol-4-yl-imidazole derivatives of formula I wherein R1, R2 and R3 are as described in the specification.

PYRAZOLO AND IMIDAZO-PYRIMIDINE DERIVATIVES

The present invention relates to novel pyrazolo- and imidazo-pyrimidine derivatives of formula (I) wherein A, D, E, L, M, Q, R1, R2 and R3 are as defined in the description and claims and to processes for their preparation, pharmaceutical compositions containing said derivatives and their use in the prevention and treatment of diseases.

Polar substitutions in the benzenesulfonamide ring of celecoxib afford a potent 1,5-diarylpyrazole class of COX-2 inhibitors

Several chemical modifications in the N1-benzenesulfonamide ring of celecoxib are presented. The series with a hydroxymethyl group adjacent to the sulfonamide was found to be the most potent modification that yielded many compounds selectively active against COX-2 enzyme in vitro.

Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: Identification of 4-[5-(4-methylphenyl)- 3(trifluoromethyl)-1h-pyrazol-1-yl]benzenesulfonamide (sc-58635, celecoxib)

A series of sulfonamide-containing 1,5-diarylpyrazole derivatives were prepared and evaluated for their ability to block cyclooxygenase-2 (COX-2) in vitro and in vivo. Extensive structure-activity relationship (SAR) work was carried out within this series, and a number of potent and selective inhibitors of COX-2 were identified. Since an early structural lead (1f, SC- 236) exhibited an unacceptably long plasma half-life, a number of pyrazole analogs containing potential metabolic sites were evaluated further in vivo in an effort to identify compounds with acceptable pharmacokinetic profiles. This work led to the identification of 1i (4-[5-(4-methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-y1]benzenesulfonamide, SC-58635, celecoxib), which is currently in phase III clinical trials for the treatment of rheumatoid arthritis and osteoarthritis.