163449-68-1

Basic information

• Product Name: 3-(4-fluorophenyl)-1-(3-hydroxyphenyl)-2-propen-1-one
• Synonyms: 3-(4-fluorophenyl)-1-(3-hydroxyphenyl)-2-propen-1-one
• CAS NO: 163449-68-1
• Molecular Formula: C15H11FO2
• Molecular Weight: 242.2450432
• Mol File: 163449-68-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(4-fluorophenyl)-1-(3-hydroxyphenyl)-2-propen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-fluorophenyl)-1-(3-hydroxyphenyl)-2-propen-1-one(163449-68-1)
• EPA Substance Registry System: 3-(4-fluorophenyl)-1-(3-hydroxyphenyl)-2-propen-1-one(163449-68-1)

Safety Data

• Hazardous Substances Data: 163449-68-1(Hazardous Substances Data)

Upstream product

• 121-71-1 3-Hydroxyacetophenone 
• 459-57-4 4-fluorobenzaldehyde 

Relevant articles and documents

Anti-cholinesterase activity of chalcone derivatives: Synthesis, in vitro assay and molecular docking study

Background: Chalcones, originated from natural product, have been broadly studied their biological activity against various proteins which at the molecular level, are responsible for the progress of the diseases in cancer (e.g. kinases), inflammation (oxi

New chalcone-3-O-glycoside derivatives: Synthesis and characterization

Seven novel carbohydrate conjugates of new chalcone-3-O-glycosides were synthesized and characterized. Starting from the substituted 3′-hydroxyarylmethylacetophenone derivatives (chalcones) with α-acetobromoglucose in anhydrous acetone were synthesized 2,

COMPOUNDS AND METHODS FOR TREATING OR PREVENTING HEART FAILURE

The present invention relates to the discovery of novel compounds that can be used to treat and/or prevent heart failure in a subject. In certain embodiments, the compounds of the invention are sulfide: quinone oxidoreductase (SQOR) inhibitors. In other e

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.

Inhibition of LPS-stimulated ROS production by fluorinated and hydroxylated chalcones in RAW 264.7 macrophages with structure-activity relationship study

Based on the importance of the previous fluorinated and/or hydroxylated chalcones studies, thirty-six compounds were designed as phenyl or hydroxyphenyl bearing fluoro, trifluoromethyl or trifluoromethoxy phenyl propenones and synthesized by applying modified Claisen-Schmidt condensation reaction as a single step. Inhibitory effects of the synthesized compounds on ROS production stimulated by LPS in RAW 264.7 macrophage were evaluated. Structure-activity relationship (SAR) study revealed that the compounds possessing para-hydroxyphenyl group combined with meta-fluoro or meta-trifluoromethyl phenyl group, and meta/para-hydroxyphenyl group combined with ortho-trifluoromethoxyphenyl group have an essential role in inhibiting the LPS-stimulated ROS production in RAW 264.7 macrophages. The most significant inhibitory effect on LPS-stimulated ROS production in RAW 264.7 macrophages was observed in compound 30 that possessed para-hydroxyphenyl group along with ortho-trifluoromethoxyphenyl group.

Indenone Derivative and Pharmaceutical Composition Comprising Same

An indenone derivative of formula (1) is effective in enhancing the activity of osteoblastic cells and inhibiting bone resorption by osteoclastic cells, and a pharmaceutical composition comprising the indenone derivative or a pharmaceutically acceptable salt thereof is useful for preventing or treating bone diseases such as osteoporosis.

INDENONE DERIVATIVE AND PHARMACEUTICAL COMPOSITION COMPRISING SAME

An indenone derivative of formula (1) is effective in enhancing the activity of osteoblastic cells and inhibiting bone resorption by osteoclastic cells, and a pharmaceutical composition comprising the indenone derivative or a pharmaceutically acceptable salt thereof is useful for preventing or treating bone diseases such as osteoporosis.

Solid-phase synthesis and biological evaluation of a parallel library of 2,3-dihydro-1,5-benzothiazepines

Solid-phase synthesis of a parallel library of 3′-hydroxy-2,3-dihydrobenzothiazepines has been carried out through [4+3] annulation of α,β-unsaturated ketones with aminothiophenol, using Wang resin as solid support. The synthesized compounds were evaluated for their potential as antibacterial, tumor inhibitors as well as acetyl- and butyrylcholinesterase inhibitors. None of the compounds showed any significant antibacterial activity. However, quite a few compounds showed significant potential as crown gall tumor inhibitors. These results reflect a strong exploratory potential in search of new benzothiazepines as source of anticancer agents. The results of the inhibition of cholinesterase revealed that benzothiazepines have a greater potential as butyrylcholinesterase inhibitors as compared to acetylcholinesterase. Moreover, the substitution of hydroxy group at C-3 in ring A led to increased activity when compared to unsubstituted- and 2′-OH substituted benzothiazepines.

Synthesis and fungicidal evaluation of novel chalcone-based strobilurin analogues

Strobilurin derivatives have become one of the most important classes of agricultural fungicide due to a novel action mode, wide fungicidal spectrum, lower toxicity toward mammalian cells, and environmentally benign characteristics. To discover new strobilurin analogues with high activity against resistant pathogens, a series of new chalcone-based strobilurin derivatives are designed and synthesized by integrating a chalcone scaffold with a strobilurin pharmacophore. The preliminary bioassay showed that some of the chalcone analogues exhibited good in vivo fungicidal activities against Pseudoperoniospora cubensis and Sphaerotheca fuliginea at the dosage of 200 μg mL-1. Two compounds, (￡)-methyl 2-[2-({3-[(￡)-3-(2- chlorophenyl)acryloyl]phenoxy}methyl)phenyl]-3-meth-oxyacrylate (1e) and (E)-methyl 2-[2-({3-[(E)-3-(3-bromophenyl)acryloyl]phenoxy}methyl)phenyl]-3- methoxyacrylate (11), were found to display higher fungicidal activities against P. cubensis (EC90 = 118.52 μg ml-1 for 1e and EC 90 = 113.64 μg mL-1 for 11) than Kresoxim-methyl (EC90 = 154.92 μg mL-1) and were identified as the most promising candidates for further study. The present work demonstrated that strobilurin analogues containing chalcone as a side chain could be used as a lead structure for further developing novel fungicides. To our knowledge, this is the first report about the syntheses and fungicidal activities of chalcone-based strobilurin derivatives.