126473-61-8

Basic information

• Product Name: 1-(4-bromophenyl)-3-(4-fluorophenyl)-2-propen-1-one
• Synonyms: 1-(4-bromophenyl)-3-(4-fluorophenyl)-2-propen-1-one
• CAS NO: 126473-61-8
• Molecular Formula: C₁₅H₁₀BrFO
• Molecular Weight: 305.1417032
• Mol File: 126473-61-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(4-bromophenyl)-3-(4-fluorophenyl)-2-propen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-bromophenyl)-3-(4-fluorophenyl)-2-propen-1-one(126473-61-8)
• EPA Substance Registry System: 1-(4-bromophenyl)-3-(4-fluorophenyl)-2-propen-1-one(126473-61-8)

Safety Data

• Hazardous Substances Data: 126473-61-8(Hazardous Substances Data)

Upstream product

• 459-57-4 4-fluorobenzaldehyde 
• 99-90-1 para-bromoacetophenone 

Downstream Products

• 98991-36-7 2-(4-Bromo-phenyl)-4-(4-fluoro-phenyl)-6-naphthalen-2-yl-pyridine 
• 1403750-32-2 (3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone 
• 1403750-47-9 (3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanone 
• 1024085-01-5 3-(4-bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole 

Relevant articles and documents

TRPV3 inhibitor and preparation method thereof

The invention discloses a TRPV3 inhibitor which is formed by sequentially connecting an R1 group, an R group and an R2 group, and the molecular structural general formula of the TRPV3 inhibitor is shown as a formula 1 in the description. The invention als

Fluorine as a robust balancer for tuning the reactivity of topo-photoreactions of chalcones and the photomechanical effects of molecular crystals

Fluorine-free chalcones and chalcones bearing different numbers of fluorine atoms have been synthesized. It is found that fluorine can tune the reactivity of photo-induced [2 + 2] cycloaddition reactions in crystals. The higher the number of fluorine atom

Aryl-4,5-dihydro-1H-pyrazole-1-carboxamide derivatives bearing a sulfonamide moiety show single-digit nanomolar-to-subnanomolar inhibition constants against the tumor-associated human carbonic anhydrases IX and XII

A series of new 3-phenyl-5-aryl-N-(4-sulfamoylphenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide derivatives was designed here, synthesized, and studied for carbonic anhydrase (CAs, EC 4.2.1.1) inhibitory activity against the human (h) isozymes I, II, and VII (cytosolic, off-target isoforms), and IX and XII (anticancer drug targets). Generally, CA I was not effectively inhibited, whereas effective inhibitors were identified against both CAs II (KIs in the range of 5.2-233 nM) and VII (KIs in the range of 2.3-350 nM). Nonetheless, CAs IX and XII were the most susceptible isoforms to this class of inhibitors. In particular, compounds bearing an unsubstituted phenyl ring at the pyrazoline 3 position showed 1.3-1.5 nM KIs against CA IX. In contrast, a subset of derivatives having a 4-halo-phenyl at the same position of the aromatic scaffold even reached subnanomolar KIs against CA XII (0.62-0.99 nM). Docking studies with CA IX and XII were used to shed light on the derivative binding mode driving the preferential inhibition of the tumor-associated CAs. The identified potent and selective CA IX/XII inhibitors are of interest as leads for the development of new anticancer strategies.

Asymmetric synthesis of new γ-butenolides: Via organocatalyzed epoxidation of chalcones

γ-Butenolides have been recognized as an important structural framework in a number of natural products and medicinally important agents. In this work we describe a new metal-free sequential strategy for the asymmetric synthesis of substituted γ-butenolides having epoxychalcones as the advanced intermediate. Using the optimized reaction conditions, we were able to carry out the three-step sequence, epoxidation, olefination and hydrolysis, with only one single chromatographic purification of the final product, furnishing new enantiomerically enriched γ-butenolides in moderate overall yield and good enantiomeric excess.

Preparation, Antiepileptic Activity, and Cardiovascular Safety of Dihydropyrazoles as Brain-Penetrant T-Type Calcium Channel Blockers

A series of dihydropyrazole derivatives was developed as potent, selective, and brain-penetrating T-type calcium channel blockers. An optimized derivative, compound 6c, was advanced to in vivo studies, where it demonstrated efficacy in the WAG/Rij rat model of generalized nonconvulsive, absence-like epilepsy. Compound 6c was not efficacious in the basolateral amygdala kindling rat model of temporal lobe epilepsy, and it led to prolongation of the PR interval in ECG recordings in rodents.

Mild and efficient reductive deoxygenation of epoxides to olefins with tin(II) chloride/sodium iodide as a novel reagent

A highly efficient and green protocol is reported for the reductive deoxygenation of organic epoxides to olefins using tin(II) chloride/sodium iodide as a novel reagent. The reaction gives an excellent yield (85-96%) in ethanol under reflux within 2-10 minutes, without affecting other functional groups. The advantages of our method are the use of inexpensive reagents, the eco-friendly and green reaction conditions, and the short reaction times and high yields.

Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach

Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.

A general, mild and efficient palladium-catalyzed 2,2,2-trifluoroethoxylation of activated aryl bromides and bromo-chalcones: Bromo-chalcones a new coupling partner in cross-coupling reaction

An efficient protocol for Pd-catalyzed 2,2,2-trifluoroethoxylation of activated aryl bromides and bromo-chalcones has been developed. We unveil a fascinating insight into the Pd-catalyzed C-O cross-coupling reaction. Pd/tBuXPhos (L1) ligand system facilitates the C-O cross-coupling reaction between 2,2,2-trifluoroethanol and activated aryl bromides at both higher (115 °C) and lower temperatures (40 °C). Unprecedentedly, this catalyst system facilitates the C-O cross-coupling reaction in short span of reaction times, generally 5-25 min (at 115 °C). The structurally simple analogue of tBuXPhos ligand so called JohnPhos (L2) ligand is also facilitated the C-O bond formation with activated aryl bromides and bromo-chalcones. Interestingly, under the optimal conditions (L1), methanol is also coupled rapidly with activated aryl bromides. These catalyst systems (L1 and L2) fail to couple electron rich aryl bromides with 2,2,2-trifluoroethanol, thus these catalyst systems allow the reductive elimination through an electronic pathway of reductive elimination. The unusual reactivity of 2,2,2-trifluoroethanol in Pd-catalyzed C-O cross-coupling reaction makes that the chemistry of fluorinated molecules is unique than that of non-fluorinated analogues. The bromo-chalcones can be used as a new coupling partner in the cross-coupling reaction.

Design, modification and 3D QSAR studies of novel 2,3-dihydrobenzo[b][1,4] dioxin-containing 4,5-dihydro-1H-pyrazole derivatives as inhibitors of B-Raf kinase

Two series of novel 2,3-dihydrobenzo[b][1,4]dioxin-containing 4,5-dihydro-1H-pyrazole derivatives C1-C15 and D1-D15 have been synthesized and evaluated for their B-Raf inhibitory and anti-proliferation activities. Compound C14 ((3-(4-bromophenyl)-5-(2-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)(2,3- dihydrobenzo[b][1,4]dioxin-6-yl)methanone) showed the most potent biological activity against B-RafV600E (IC50 = 0.11 μM) and WM266.4 human melanoma cell line (GI50 = 0.58 μM), being comparable with the positive control Erlotinib and more potent than our previous best compound, while D10 ((2,3-dihydrobenzo[b][1,4]dioxin-2-yl)(5-(3- fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone) performed the best in the D series (IC50 = 1.70 μM; GI50 = 1.45 μM). The docking simulation was performed to analyze the probable binding models and poses and the QSAR model was built for reasonable design of B-Raf inhibitors in future. The introduction of 2,3-dihydrobenzo[b][1,4]dioxin structure reinforced the combination of our compounds and the receptor, resulting in progress of bioactivity.