350474-66-7

Usage

Main properties

1. Chemical compound
2. Belongs to the group of prop-2-en-1-ones
3. Contains a ketone group attached to a propene
4. Consists of a three-carbon chain

Specific content

1. 3-(4-bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-one
2. Ketone group at the first carbon
3. Phenyl groups at the second and third carbons
4. Contains 4-bromophenyl and 4-fluorophenyl substitutions
5. Used in synthesis of pharmaceuticals, agrochemicals, and materials
6. Used in research and development in chemical and pharmaceutical industries

Upstream product

• 766-98-3 1-ethynyl-4-fluorobenzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 403-42-9 1-(4-fluorophenyl)ethanone 

Downstream Products

• 1366267-77-7 2-(5-(4-bromophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one 
• 642033-21-4 2-amino-3-cyano-6-(4-bromophenyl)-4-(4-fluorophenyl)pyridine 
• 7397-22-0 1-(4-fluorophenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one 
• 1415320-96-5 3-(4-bromophenyl)-5-(4-fluorophenyl)-1H-pyrazole 

Relevant academic research and scientific papers

Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system

An efficient and sustainable protocol for the hydration of alkynes has been developed under metal/acid/catalyst/ligand-free conditions in a water/ethyl lactate mixture. The hydrogen-bond network in the ethyl lactate and water mixture plays a crucial and decisive role in activating the alkynes for hydration to afford the corresponding methyl ketones. This strategy gives the Markovnikov (ketone) addition product selectively over other possible products. The essential role of hydrogen bonding has been confirmed by experimental and theoretical techniques. A probable mechanism has been suggested by various control tests. The efficacy of the method has been further explored for the competent production of value-added α,β-unsaturated carbonyl compounds through the reaction of aldehydes with alkynes as ketonic surrogates. The environmentally benign hydration method takes place under mild conditions, has broad functional-group compatibility, and uses the ethyl lactate/water (1:3) medium as a “green alternative” in the absence of any hazardous, harmful, or expensive substances.

Pharmacophore hybridization approach to discover novel pyrazoline-based hydantoin analogs with anti-tumor efficacy

In search for new and safer anti-cancer agents, a structurally guided pharmacophore hybridization strategy of two privileged scaffolds, namely diaryl pyrazolines and imidazolidine-2,4-dione (hydantoin), was adopted resulting in a newfangled series of compounds (H1-H22). Herein, a bio-isosteric replacement of “pyrrolidine-2,5-dione” moiety of our recently reported antitumor hybrid incorporating diaryl pyrazoline and pyrrolidine-2,5-dione scaffolds with “imidazoline-2,4-dione” moiety has been incorporated. Complete biological studies revealed the most potent analog among all i.e. compound H13, which was at-least 10-fold more potent compared to the corresponding pyrrolidine-2,5-dione, in colon and breast cancer cells. In-vitro studies showed activation of caspases, arrest of G0/G1 phase of cell cycle, decrease in the expression of anti-apoptotic protein (Bcl-2) and increased DNA damage. In-vivo assay on HT-29 (human colorectal adenocarcinoma) animal xenograft model unveiled the significant anti-tumor efficacy along with oral bioavailability with maximum TGI 36% (i.p.) and 44% (per os) at 50 mg/kg dose. These findings confirm the suitability of hybridized pyrazoline and imidazolidine-2,4-dione analog H13 for its anti-cancer potential and starting-point for the development of more efficacious analogs.

Synthesis and Antiproliferative Activity of Novel Hydrazono Thiazolidene and Thiazole Derivatives Bearing Rhodanine Moiety

Abstract: Some new fluoro-heterocyclic compounds containing thiazole and pyridine moities have been synthesized and studied for their antiproliferative activity. Thiazole derivatives have been synthesized by the reaction of alpha-halo carbonyl compounds with thiosemicarbazones. Some pyridine derivatives have been synthesized by the reaction of chalcone with cyanothioacetamide and/or malononitrile. Spectroscopic methods have been used for elucidating molecular structures of the products. Cytotoxic activity of several derivatives has been tested against human breast cancer (MCF-7), human colon cancer (HCT-116) and human liver cancer (Hep-G2) by the SRB method. Most of compounds exhibit mild effect on the tested cell lines. One of thiazolidin-4-one derivatives has been characterized by moderate to strong effect on MCF-7 cell line.

Pyrazoline thiazole derivative as well as preparation method and application thereof

The invention discloses a pyrazoline thiazole derivative as well as a preparation method and application thereof. The pyrazoline thiazole derivative has the following general formula shown in the specification, wherein R1 is selected from 4-Br, 4-F, 4-CH3

Design, synthesis, and SAR study of novel 4,5-dihydropyrazole-Thiazole derivatives with anti-inflammatory activities for the treatment of sepsis

Systemic inflammatory response syndrome is a major feature of sepsis which is one of the major causes of death worldwide. It has been reported that 3,5-diaryl-4,5-dihydropyrazole and thiazole derivatives have many biological functions, especially in the aspect of anti-inflammation. According to the strategy of pharmacophore combination, we introduced thiazole moiety into dihydropyrazole skeleton to design and synthesize a novel series of 2-(3,5-diphenyl-4,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole derivatives, and evaluated their anti-inflammatory activities for sepsis treatment. Preliminary structure?activity relationship (SAR) analysis was conducted by their inhibitory activities against nitric oxide (NO) release in LPS-induced RAW264.7 cells, and the optimal compound E26 exhibited more potent anti-inflammatory activity than the positive control treatment indomethacin and dexamethasone. In further mechanism study, our results showed that compound E26 significantly suppressed the production of interleukin-1β (IL-1β), tumor necrosis factor-α (TNF-α), NO and inhibited the expressions of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2) through blocking MAPKs signaling pathway. In addition, in vivo administration of compound E26 resulted in a significant improvement of LPS-induced sepsis in C57BL/6J mice, with reducing toxicity in multiple organs. Taken together, this study demonstrated the compound E26 could be a promising agent for the treatment of sepsis.

Synthesis and theoretical study of a series of 3,5-disubstitutes pyrazoles

In this work, we proposed the synthesis of a series of pyrazoles derivatives with different substituents on the aromatic rings. We aim to evaluate their influence on the reactivity of the compounds in reactions of α,β-unsaturated chalcones and sulfonyl hydrazide catalyzed by iodine. In order to explain their high and low yields, or the impossibility of obtaining some compounds by applied synthetic methodology, Density Functional Theory (DFT) calculations were performed. The reaction Gibbs free energy (ΔG) as well as the energy gap of the HOMO-LUMO frontier orbitals (ΔE) of some selected reactants could explain qualitatively the experimental observations in terms of synthesis yield. In this way, we believe that the chemical nature of aromatic ring substituents is relevant for the reactivity of the starting materials as well as the formation of the desired products.

The Solvatofluorochromism of 2,4,6-Triarylpyrimidine Derivatives

Seven new 2,4,6-triarylpyrimidines were synthesized and their solvatofluorochromism investigated in 12 solvents and in an aqueous micellar solution of reduced Triton X-100. A multiparametric analysis of their emission band showed that the solvent dipolari

Synthesis and structure-activity relationships of 4-morpholino-7,8-dihydro-5h-thiopyrano[4,3-d] pyrimidine derivatives bearing pyrazoline scaffold

Phosphatidylinositol 3-kinase/Protein kinase B/Mammalian target of rapamycin (PI3K/Akt/mTOR) signaling pathway is abnormally active in the growth and proliferation of cancer cells. The inhibition of PI3K kinase can effectively block the conduction of sign

Synthesis, spectroscopic and computational characterization of the tautomerism of pyrazoline derivatives from chalcones

In the present study a series of novel pyrazolines derivatives has been synthesized, and their structures assigned on the basis of FT-Raman, 1H and 13C NMR spectral data and computational DFT calculations. A joint computational study using B3LYP/6-311G(2d,2p) density functional theory and FT-Raman investigation on the tautomerism of 3-(4-substituted-phenyl)-4,5-dihydro-5-(4-substituted-phenyl)pyrazole-1-carbothioamide and 3-(4-substituted-phenyl)-4,5-dihydro-5-(4-substituted-phenyl)pyrazole-1-carboxamide are presented. The structures were characterized as a minimum in the potential energy surface using DFT. The calculated Raman and NMR spectra were of such remarkable agreement to the experimental results that the equilibrium between tautomeric forms has been discussed in detail. Our study suggests the existence of tautomers, the carboxamide/carbothioamide group may tautomerize, in the solid state or in solution. Thermodynamic data calculated suggests that the R(CS)NH2 and R(CO)NH2 species are more stable than the R(CNH)SH and R(CNH)OH species. Additionally, results found for the 1H NMR shifting, pointed out to which structure is present.

Design, synthesis, and pharmacological evaluation of new pyrazoline derivatives

In the present investigation, a new series of pyrazoline derivatives has been synthesized by the reaction of chalcones with hydrazine derivatives like hydrazine hydrate and phenyl hydrazines in the presence of different aliphatic acids. The chemical struc