97727-86-1

Basic information

• Product Name: 4'-hydroxy-2-fluorochalcone
• Synonyms: 4'-hydroxy-2-fluorochalcone
• CAS NO: 97727-86-1
• Molecular Weight: 242.25
• Mol File: 97727-86-1.mol

Chemical Properties

• CAS DataBase Reference: 4'-hydroxy-2-fluorochalcone(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-hydroxy-2-fluorochalcone(97727-86-1)
• EPA Substance Registry System: 4'-hydroxy-2-fluorochalcone(97727-86-1)

Safety Data

• Hazardous Substances Data: 97727-86-1(Hazardous Substances Data)

Upstream product

• 446-52-6 2-Fluorobenzaldehyde 
• 99-93-4 4-Hydroxyacetophenone 
• 1453488-78-2 C₂₀H₁₉FO₃ 
• 16162-69-9 1-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone 

Downstream Products

• 1453487-91-6 C₁₆H₁₅FN₂O 

Relevant articles and documents

Biological activity evaluation and action mechanism of chalcone derivatives containing thiophene sulfonate

A series of novel chalcone derivatives containing a thiophene sulfonate group were designed and synthesized. The structures of all title compounds were determined by 1H-NMR, 13C-NMR and HRMS. Antibacterial bioassays indicated that, compound 2l demonstrated excellent antibacterial activities against Xanthomonas axonopodis pv. citri (Xac), with an EC50 value of 11.4 μg mL-1, which is significantly superior to those of bismerthiazol (BT) (51.6 μg mL-1) and thiodiazole-copper (TC) (94.7 μg mL-1). Meanwhile, the mechanism of action of compound 2l was confirmed by using scanning electron microscopy (SEM). In addition, compound 2e showed remarkable inactivation activity against Tobacco mosaic virus (TMV), with an EC50 value of 44.3 μg mL-1, which was superior to that of ningnanmycin (120.6 μg mL-1). Microscale thermophoresis (MST) also showed that the binding of compounds 2e and 2h to Tobacco mosaic virus coat protein (TMV-CP) yielded Kd values of 0.270 and 0.301 μmol L-1, which are better than that of ningnanmycin (0.596 μmol L-1). At the same time, molecular docking studies for 2e and 2h with TMV-CP (PDB code: 1EI7) showed that the compound was embedded well in the pocket between the two subunits of TMV-CP in each case. These results suggested that chalcone derivatives containing a thiophene sulfonate group may be considered as activators in the design of antibacterial and antiviral agents.

Design, synthesis, and antiviral activities of 1,5-benzothiazepine derivatives containing pyridine moiety

In our previous work, a series of novel benzothiazepine derivatives containing pyridine moiety were successfully synthesized through chalcone 1,3-dipolar cycloaddition and determined their antiviral activity against tobacco mosaic virus (TMV). Bioassay results indicated that most of these target compounds exhibited improved curative, protection, and inactivation activity in?vivo than the commercial agent ningnanmycin. Particularly, compound 3m exhibited marked curative activity against TMV, with an EC50value of 352.2?μM, which was even better than that of ningnanmycin. The compound was identified as the most promising candidate for inhibiting plant virus and an excellent compound with antiviral activities against TMV. Structure–activity relationship experiment indicated that the 1,5-benzothiazepine moiety is crucial for potent anti-TMV activity.

Synthesis, structural and thermal characterizations, dielectric properties and in vitro cytotoxic activities of new 2,2,4,4-tetra(4′-oxy-substituted-chalcone)-6,6-diphenylcyclotriphosphazene derivatives

In this study, we aimed to investigate the relationship between the cytotoxic and dielectric properties of newly synthesized 2,2,4,4-tetra(4′-oxy-substituted-chalcone)-6,6-diphenylcyclotriphosphazene derivatives (3–10). Firstly, 2,2,4,4-tetrachloro-6,6-di

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.

Synthesis, structural characterization and anti-carcinogenic activity of new cyclotriphosphazenes containing dioxybiphenyl and chalcone groups

2,2-Dichloro-4,4,6,6-bis[spiro(2′,2″-dioxy-1′,1″-biphenylyl]cyclotriphosphazene (2) was synthesized from hexachlorocyclotriphosphazene (HCCP) and 2,2′-dihydroxybiphenyl. The mixed substituent chalcone/dioxybiphenyl cyclophosphazenes (2a-h) were obtained from the reactions of (2) with hydroxy chalcone compounds in K2CO3/acetone system. The chalcone-cyclophosphazene compounds were characterized by elemental analysis, FT-IR, 1H, 13C, 31P NMR techniques. In vitro anti-carcinogenic activities of all compounds were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Anti-carcinogenic activity of the compounds (2a-h) against androgen-dependent (LNCaP) and independent (PC-3) human prostate cancer cell lines were investigated. Our results indicate that the chalcone-phosphazene compounds (2a-h) have anti-carcinogenic activity on PC-3 and LNCaP cell lines (p 0.05). The effective dose of the compounds was determined as 100 μM.

Synthesis, characterization and dielectric properties of phosphazenes containing chalcones

The new hexasubstitue-cyclophosphazene compounds containing chalcone derivatives (2-11) were obtained from the reactions of hexachlorocyclotriphosphazene (1) with several hydroxy chalcones in K 2CO3/acetone system. All products were generally obtained in high yields. The structures of the compounds were defined by elemental analysis, FT-IR, 1H, 13C and 31P NMR spectroscopy. Dielectric measurements for phosphazenes containing chalcone compounds (5-8) were carried out by means of an impedance analyzer as a function of temperature and frequency. Dielectric properties of samples prepared in a plate form were measured at room temperature over the frequency range 50 Hz to 2 kHz and given as compared with each other.

Design, synthesis, and in vitro hMAO-B inhibitory evaluation of some 1-methyl-3,5-diphenyl-4,5-dihydro-1H-pyrazoles

A series of 1-methyl-3,5-diphenyl-4,5-dihydro-1H-pyrazoles (3a-k and 4a-u) were designed, synthesized, and evaluated for their inhibitory efficacy towards the two hMAO isoforms. Most of the derivatives were found to be potent and selective hMAO-B inhibitors. In particular, derivative 3g showed greater hMAO-B affinity than selective inhibitor selegiline coupled with high selectivity index (SI = 145). The most selective hMAO-B inhibitor was the 3-methyl analogue 3f with an SI higher than 909.