7397-22-0

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-Fluorophenyl)-3-(4-hydroxyphenyl)-2-propen-1-one is used as a pharmaceutical compound for its potential biological activities. The presence of the fluorophenyl and hydroxyphenyl groups may contribute to its therapeutic properties, making it a candidate for further study and development in drug discovery.
Used in Materials Science:
In the field of materials science, 1-(4-Fluorophenyl)-3-(4-hydroxyphenyl)-2-propen-1-one is used for its structural characteristics. Its unique molecular arrangement and functional groups may offer novel properties and applications in the development of advanced materials.

InChI:InChI=1/C15H11FO2/c16-13-6-4-12(5-7-13)15(18)10-3-11-1-8-14(17)9-2-11/h1-10,17H/b10-3+

Upstream product

• 350474-66-7 3-(4-bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-one 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 1246618-05-2 4-(1-acetyl-3-4'-fluorophenyl-2-pyrazolin-5-yl)phenol 
• 748771-26-8 4-[5-(4-fluorophenyl)isoxazol-3-yl]phenol 
• 1603988-60-8 2-(4-(5-(4-fluorophenyl)isoxazol-3-yl)phenoxy)acetic acid 
• 1462341-39-4 C₂₁H₁₅FN₂O 
• 1462341-50-9 1-phenyl-3-(4-fluorophenyl)-5-(4-(2-ethanoloxy)phenyl)-1H-pyrazole 

Relevant academic research and scientific papers

Dependence of thermotropic mesomorphism on varying rigidity of central bridge in liquid crystals

A novel liquid crystalline(LC) homologous series of chalconyl esters: RO-C6H4-COO-C6H4-CH = CH-CO-C6H4F has been synthesized and studied with a view to understanding and establishing the relationship between thermotropic LC properties and molecular structure with reference to varying molecular rigidity due to linking groups. The novel homologous series consists of eleven members (C1 to C16). C1 and C2 homologues are nonliquid crystals (NLC) and the rest of the homologues are enantiotropically nematic (C3 to C16). The smectogenic character, either in enantiotropic or monotropic manner is totally absent for a series. Transition temperatures and textures of nematic phase were determined by an optical polarizing microscope (POM) equipped with a heating stage. Textures of the nematic phase are threaded or Schlieren. The analytical, thermal and spectral data support the molecular structures. Cr-N/I and N-I transition curves behaved in normal manner except for the C14 homologue. N-I transition curve exhibits an odd- even effect with a negligible deviating effect from the C10 homologue. Thermal stability for the nematic is 105.2°C and mesophase lengths range from 06.0°C to 46.0°C at C8 and C14 homologues respectively. The group efficiency order derived for nematic from the comparative study of present novel series with structurally similar analogous series on the basis of thermal stability as under.

Aldoxime- and hydroxy-functionalized chalcones as highly potent and selective monoamine oxidase-B inhibitors

A panel of 30 chalcone derivatives, including 19 aldoxime-chalcone ethers (ACE), and 11 hydroxyl?chalcones (HC), previously synthesized using a Pd-catalyzed C–O cross-coupling method were evaluated for their inhibitory activities against monoamine oxidases (MAOs), cholinesterases (ChEs), and β-secretase (BACE-1). HC6 was the most potent inhibitor of MAO-B with an IC50 value of 0.0046 μM and a selectivity index (SI) of 1,113. HC3 also potently inhibited MAO-B (IC50 = 0.0067 μM) and had the highest SI (1,455). ACE7 and ACE15 were also potent MAO-B inhibitors (IC50 = 0.012 and 0.018 μM, respectively), with SIs of 260 and 1,161, respectively. HC3 and HC6 were reversible competitive inhibitors of MAO-B, with Ki values of 0.0036 and 0.0013 μM, respectively. A structure–activity relationship revealed that methyl and fluorine substituents contributed to increasing both inhibition and selectivity. ACE7 was the most effective inhibitor of MAO-A (IC50 = 1.49 μM), followed by ACE3 (IC50 = 3.75 μM). No compounds effectively inhibited AChE, BChE, or BACE-1. A docking simulation showed that the ligand efficiency and docking scores of HC3 and HC6 toward MAO-B were consistent with the experimental IC50 values. These results suggest that HC3 and HC6 can be considered promising candidates for the treatment of neurological disorders.

Antibacterial and anti-inflammatory activity of valproic acid-pyrazole conjugates as a potential agent against periodontitis

Periodontitis is a serious global concern. Therefore, in the present study, we intend to synthesize novel valproic-acid pyrazole conjugates as a novel agent against periodontitis. The molecules were developed in a facile synthetic route and obtained in ex

Hydroxyl- and Halogen-containing Chalcones for the Inhibition of LPS-stimulated ROS Production in RAW 264.7 Macrophages: Design, Synthesis and Structure–Activity Relationship Study

Oxidative stress due to overproduction of reactive oxygen species (ROS) plays a major role in inflammation, cancer, and neurodegenerative disorders. In this study, 60 chalcone derivatives with fluorine (F), trifluoromethyl (CF3), trifluoromethoxy (OCF3), chlorine (Cl), and bromine (Br) in ring A and with or without hydroxy (OH) in ring B were designed, synthesized, and screened for inhibitory activity against lipopolysaccharide (LPS)-stimulated ROS production in RAW 264.7 macrophages. Structure–activity relationship study revealed the importance of a hydroxyl moiety in ring B for enhancing inhibitory activity of ROS production. Furthermore, a hydroxyl group at the ortho-position is more essential for inhibition of ROS production followed by meta- and para-positions. Among all, compound 27 that contains para-chlorine moiety in ring A and ortho-hydroxy in ring B displayed the strongest inhibitory activity (IC50 = 3.42 μM) against LPS-stimulated ROS production in RAW264.7 macrophages.

Structure-activity relationship with pyrazoline-based aromatic sulfamates as carbonic anhydrase isoforms I, II, IX and XII inhibitors: Synthesis and biological evaluation

Four new series of aromatic sulfamates were synthesized and investigated for the inhibition of four human (h) isoforms of zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1), hCA I, II, IX, and XII. The reported derivatives, obtained by a sulfamoylation reaction of the corresponding phenolic precursors, bear 3,5-diarylpyrazoline moieties as spacers between the benzenesulfamate fragment which binds the zinc ion from the active site, and the tail of the inhibitor. Pyrazolines are biologically privileged scaffolds, endowed with versatile biological activity, such as an anti-proliferative action. The derivatives were tested for the inhibition of the cytosolic, hCA I and II (off target isoforms) and the trans-membrane, tumor-associated hCA IX and XII enzymes (anticancer drug targets). Generally, hCA I was not effectively inhibited, whereas many low nanomolar inhibitors were evidenced against hCA II (KIs in the range of 0.42–90.1 nM), IX (KIs in the range of 0.72–63.6 nM), and XII (KIs in the range of 0.88–85.2 nM). The best substitution fragments at the pyrazoline ring included for CA II a 4-sulfamic group on the 3-aryl and halogens on the 5-aryl or a methoxy group on the 3-aryl and a 4-sulfamate group on the 5-aryl; for CA IX and CA XII they included the sulfamic group on the 3- or 4-position of the 5-aryl and an electronwithdrawing group on the 4-postion of the 3-aryl ring.

Synthesis and biological evaluation of coumarin clubbed thiazines scaffolds as antimicrobial and antioxidant

A new series of 4-methyl-6-nitro-2-oxo-2H-chroman-7yl-2-(4-(4-fluorophenyl)-6-phenyl-2H-1,3-thiazin-2-yl-amino)acetates 5a–j were synthesized from 6-nitro-4-methyl coumarinyl chloroacetate (5) and 2-amino thiazines (IIIa–j). The structure of the final compounds was adequately confirmed via spectroscopic techniques (IR, 1H NMR, 13C NMR, Mass) and characterization of physical properties. Final compounds were screened for their antimicrobial, antitubercular, and antioxidant activities. Compounds 5c and 5h found to have antibacterial potency against E. coli with MIC values 50 μg/mL compared to standard drugs. Compound 5d demonstrated better antifungal potency (MIC = 200 μg/mL) against C. albicans when compared with griseofulvin. Compounds 5b and 5h found to be encouraging antitubercular (MIC = 62.5 μg/mL with 98–99% inhibition) against M. tuberculosis H37Rv. The newly synthesized 5h and 5b were appeared to have high radical scavenging efficacies as 33.99 ± 0.301 and 35.35 ± 0.470 μg/mL ± SD of IC50 values, respectively, in DPPH and ABTS bioassay.

Microwave-assisted synthesis and bioevaluation of new sulfonamides

In this study, 4-[5-(4-hydroxyphenyl)-3-aryl-4,5-dihydro-1H-pyrazol-1-yl]benzenesulfonamide derivatives (8-14) were synthesized for the first time by microwave irradiation and their chemical structures were confirmed by 1H NMR, 13C N

A Green, Solvent-Free, Microwave-Assisted, High-Yielding YbCl3Catalyzed Deprotection of THP/MOM/Ac/Ts Ethers of Chalcone Epoxide and 2′-Aminochalcone and Their Sequel Cyclization

Under microwave and solvent-free conditions, YbCl3efficiently catalyzed the deprotection of tetrahydropyran-2-yl, methoxymethyl (MOM), acetyl, and tosyl groups and sequel cyclization of chalcone epoxide to 2-hydroxyindanone and 2′-aminochalcone to aza-flavanone. The reaction afforded the products in excellent yield (78–99%) at 850 W microwave heating within 1–5 min under eco-friendly conditions. The merits of the presented protocol include high yield, use of microwave irradiation, solvent-free condition, catalyst reusability, and no need for purification with column chromatography. The present method is very much milder but more advanced than those reported earlier.

Synthesis of some novel substituted phenylisoxazol phenoxy 2-methylpropanoic acids and there in vivo hypolipidemic activity

The novel series of phenylisoxazol phenoxy 2-methylpropanoic acid derivatives were synthesized and evaluated for their in vivo hypolipidemic activity by triton WR-1339-induced hyperlipidemia in rats. The newly synthesized compounds 5a and 5i showed significant decrease in the serum TCH, TG, LDL and VLDL along with an increase in serum HDL levels as compared to standard drug Fenofibrate. The treated groups also showed significant decrease in the atherogenic index, TC:HDL risk ratios compared to cholesterol-induced hyperlipidemic control group. These molecules indeed have the potential to be developed as antihypolipidemic molecules.

Highly efficient deprotection of phenolic tetrahydropyranyl and methoxymethyl ethers and sequel cyclization to indanones using Sn(IV)Cl 4 catalyst

Sn(IV)Cl4 catalyst provided a rapid and efficient deprotection method for the phenolic THP and MOM ethers and sequel intramolecular Friedel-Crafts alkylation reaction of THP and MOM protected chalcone epoxides under mild conditions. The reaction took 2-3 min to give the products in excellent yield (90-98%) at 0 °C without affecting the other functional groups.