347-93-3

Usage

Chemical Properties

LIGHT BROWN TO ORANGE-BROWN CRYSTALLINE POWDER

Upstream product

• 462-06-6 fluorobenzene 
• 625-36-5 2-chloropropionyl chloride 
• 460-00-4 1-Bromo-4-fluorobenzene 

Downstream Products

• 132428-02-5 1-(4-Fluorophenyl)-3-([N-[4-(2,2,2-trifluoro-1-hydroxy)-1-(trifluoromethyl)ethyl]phenyl]amino)-1-propanone 
• 143667-22-5 3-Decylamino-1-(4-fluoro-phenyl)-propan-1-one 
• 1481-32-9 6-fluoroindan-1-one 
• 31736-75-1 3-chloro-1-(4-fluorophenyl)propan-1-ol 
• 51594-59-3 1-(4-fluorophenyl)-2-propen-1-one 
• 200004-39-3 (R)-3-chloro-1-(4-fluorophenyl)propan-1-ol 
• 200004-40-6 (S)-3-chloro-1-(4-fluorophenyl)propan-1-ol 
• 143667-17-8 3-(Cyclohexylmethyl-amino)-1-(4-fluoro-phenyl)-propan-1-one 
• 143667-21-4 1-(4-Fluoro-phenyl)-3-octadecylamino-propan-1-one 
• 37155-08-1 1-(4-fluorophenyl)-3-(4-methoxyphenylamino)propan-1-one 

Relevant academic research and scientific papers

I2-Promoted Intramolecular Oxidative Cyclization of Butenyl Anilines: A Facile Route to Benzo[b]azepines

A metal-free approach for the synthesis of seven-membered N-heterocycles has been developed by the I2-promoted intramolecular cross-coupling/annulation of butenyl anilines. This cyclization reaction involves C?H activation and C?C bond formation and exhibits good functional group tolerance. A series of benzo[b]azepine derivatives are obtained in moderate to good yields.

Structure-Kinetic Profiling of Haloperidol Analogues at the Human Dopamine D2 Receptor

Haloperidol is a typical antipsychotic drug (APD) associated with an increased risk of extrapyramidal side effects (EPSs) and hyperprolactinemia relative to atypical APDs such as clozapine. Both drugs are dopamine D2 receptor (D2R) antagonists, with contrasting kinetic profiles. Haloperidol displays fast association/slow dissociation at the D2R, whereas clozapine exhibits relatively slow association/fast dissociation. Recently, we have provided evidence that slow dissociation from the D2R predicts hyperprolactinemia, whereas fast association predicts EPS. Unfortunately, clozapine can cause severe side effects independent of its D2R action. Our results suggest an optimal kinetic profile for D2R antagonist APDs that avoids EPS. To begin exploring this hypothesis, we conducted a structure-kinetic relationship study of haloperidol and revealed that subtle structural modifications dramatically change binding kinetic rate constants, affording compounds with a clozapine-like kinetic profile. Thus, optimization of these kinetic parameters may allow development of novel APDs based on the haloperidol scaffold with improved side-effect profiles.

Synthesis and Evaluation of 2-Azetidinone and 1H-Pyrrole-2,5-dione Derivatives as Cholesterol Absorption Inhibitors for Reducing Inflammation Response and Oxidative Stress

Excess lipid accumulation can initiate the development and progression of atherosclerotic lesions, thus eventually leading to cardiovascular disease. Lipid-lowering medication therapy is one of the cornerstones of cardiovascular disease therapy. On the basis of the cholesterol absorption inhibitor ezetimibe, we successfully synthesized seven 2-azetidinone derivatives and eighteen 1H-pyrrole-2,5-dione derivatives. Most of the new compounds significantly inhibited cholesterol uptake in vitro. In addition, one of the most active inhibitors, 3-(4-fluorophenyl)-1-[(3S)-3-hydroxy-3-(4-hydroxyphenyl)propyl]-4-(4-hydroxyphenyl)-1H-pyrrole-2,5-dione (14q), showed no cytotoxicity in L02 and HEK293T cell lines. Further evaluation indicated that 14q inhibited considerably the amount of TNF-α, ROS, MDA, and LDH in vitro. Therefore, 14q might be a novel cholesterol absorption inhibitor.

A combined computational and experimental investigation of the oxidative ring-opening of cyclic ethers by oxoammonium cations

The propensity of oxoammonium cations to facilitate the oxidative ring-opening of cyclic ethers to their corresponding distal hydroxy ketones is investigated. The reaction has been evaluated using experimental and computational methods to gain deeper insight into trends in reactivity.

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.

Properties and structure of two fluorinated 1,10-phenanthrolines

We report the synthesis, X-ray structure, absorbance and emission of 4,7-bis(4-fluorophenyl)-1,10-phenanthroline and 4,7-bis-(4′-trifluoromethyl-biphenyl-4-yl)-1,10-phenanthroline. 4,7-Bis(4-fluorophenyl)-1,10-phenanthroline was synthesized by successive Skraup reactions and features absorbance at 274 nm and emission at 384 nm while 4,7-bis-(4′-trifluoromethyl-biphenyl-4-yl)-1,10-phenanthroline featured absorbance at 283 nm and emission at 400 nm. The structures show molecular stacking of the phenyl groups and phenanthroline structure and longitudinal fluorine atom associations within the crystal lattice. Furthermore, the three fused rings of the 4,7-bis(4-fluorophenyl)-1,10-phenanthroline unit exhibited torsion up to 13.97(9)° throughout the crystal lattice whereas no torsion is observed for 4,7-bis-(4′-trifluoromethyl-biphenyl-4-yl)-1,10-phenanthroline.

PROTEIN CROSSLINKING INHIBITOR AND USE OF THE SAME

The present invention relates to: a ketone compound having transglutaminase-inhibiting activity, which is represented by the following Formula 1, 2, or 3: wherein R1 is a substituted or unsubstituted aryl or heterocyclyl group, R2, R3, and R4 are hydrogen atoms, n is 2, X is halogen, R5 and R6 independently represent a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl, aryl, or aralkyl group, wherein R5 and R6 are not hydrogen atoms at the same time, or R5 and R6 may be taken together to form a saturated or unsaturated and substituted or unsubstituted heterocyclyl group containing a nitrogen atom (N); an inhibitor of protein crosslinking comprising the compound; and a composition for preventing or treating a protein-crosslinking causative disease, which comprises the compound or the protein crosslinking inhibitor.

PREPARATION OF FIPAMEZOLE

The application relates to processes for preparing fipamezole and its pharmaceutically acceptable salts, and intermediates thereof. It also provides intermediate compounds of Formula III and Formula IV, and processes for their preparation.

1-[(3-Aryloxy-3-aryl)propyl]-1H-imidazoles, new imidazoles with potent activity against Candida albicans and dermatophytes. Synthesis, structure-activity relationship, and molecular modeling studies

New 1-[(3-aryloxy-3-aryl)propyl]-1H-imidazoles were synthesized and evaluated against Candida albicans and dermatophytes in order to develop structure-activity relationships (SARs). Against C. albicans the new imidazoles showed minimal inhibitory concentrations (MICs) comparable to those of ketoconazole, miconazole, and econazole, and were more potent than fluconazole. Several derivatives (10, 12, 14, 18-20, 24, 28, 29, 30, and 34) turned out to be potent inhibitors of C. albicans strains resistant to fluconazole, with MIC values less than 10 μg/mL. Against dermatophytes strains, compounds 20, 25, and 33 (MIC ≤ 5 μg/mL) were equipotent to ketoconazole, econazole, and miconazole. SARs of imidazoles 10-44 were rationalized with reasonable accuracy by a previously developed quantitative pharmacophore for antifungal agents.

Imidazole analogues of fluoxetine, a novel class of anti-Candida agents

Imidazole analogues of fluoxetine have been obtained by replacing the methylamino terminus of aminopropane chain with the imidazole ring. The newly designed imidazoles showed potent anti-Candida activity, superior to those of miconazole and other antifungal agents of clinical interest. 1-(4-Chlorophenyl)-l-(2,4-dichlorophenoxy)-3-(1H-imidazol-1-yl)propane (16), the most active among test imidazoles, Was about 2-fold more active and as much less cytotoxic than miconazole. High increase of activity was observed with methyl, nitro, fluorine, and chlorine (Cl > F > CH3 > NO2 > CF3).