86293-53-0

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-1-(4-chlorophenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one is used as a pharmaceutical drug candidate for its potential antioxidant, anti-inflammatory, and anticancer properties. Its biological activities make it a promising compound for the development of new drugs to treat various diseases and conditions.
Used in Biochemistry Research:
(2E)-1-(4-chlorophenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one is used as a fluorescence probe for the detection of biologically relevant molecules. Its potential as a fluorescence probe allows researchers to study the interactions and mechanisms of various biological processes, contributing to the advancement of biochemistry and related fields.

Upstream product

• 99-91-2 para-chloroacetophenone 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 1392402-37-7 C₂₃H₁₇ClN₄O 
• 1392402-38-8 C₂₉H₂₁ClN₆O₂ 
• 1392402-39-9 C₂₈H₂₀ClN₇O₂ 
• 215257-63-9 4-(4'-chlorophenyl)-6-(4''-hydroxyphenyl)-2-aminopyrimidine 
• 1375113-49-7 4-(2-(4-chlorophenyl)-6-(thiophen-3-yl)pyridin-4-yl)phenol 
• 1375113-51-1 4-(6-(4-chlorophenyl)-[2,2'-bipyridin]-4-yl)phenol 
• 1375113-47-5 4-(2-(4-chlorophenyl)-6-phenylpyridin-4-yl)phenol 
• 1375113-48-6 4-(2-(4-chlorophenyl)-6-(thiophen-2-yl)pyridin-4-yl)phenol 
• 1375113-52-2 4-(6-(4-chlorophenyl)-2,3'-bipyridin-4-yl)phenol 
• 1375113-53-3 4-(6-(4-chlorophenyl)-2,4'-bipyridin-4-yl)phenol 
• 1375113-50-0 4-(2-(4-chlorophenyl)-6-(furan-2-yl)pyridin-4-yl)phenol 

Relevant academic research and scientific papers

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.

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

Dependence of liquid crystallinity on molecular rigidity

A novel homologous series of liquid crystals (LC) of chalconyl derivatives is synthesized and studied with a view to understanding and establishing the effects of molecular structure on liquid crystal properties. The novel series consists of 12 homologues. Nematogenic LC property commences from C3 and continues up to C14 and the smectogenic mesophase is exhibited from C4 to C16. The C3 homologue is a monotropic nematic and the rest of the homologues are enantiotropically smectic and nematic or only smectic (C16). Transition curves Cr-Sm, Sm-N, Cr-I, and N-I behave in normal manner with exhibition of odd-even effect, showing phase behaviors of the series.

Synthesis, in Vitro, and in Vivo Biological Evaluation and Molecular Docking Analysis of Novel 3-(3-oxo-substitutedphenyl-3-)4-(2-(piperidinyl)ethoxy)phenyl)propyl)-2H-chromen-2-one Derivatives as Anti-breast Cancer Agents

The analogs of coumarin-chalcones have been reported to exhibit antineoplastic, anti-allergic, antihepatoprotective, and estrogenic activity. Herein, we have reported 3-(3-oxo-substitutedphenyl-3-)4-(2-(piperidinyl)ethoxy)phenyl)propyl)-2H-chromen-2-one derivatives as a new class of compounds that exhibit selectivity for ER-α binding along with antiproliferative and cytotoxic activity on human breast cancer cell line. The active compounds which show prominent activity against estrogen receptor-alpha-positive (ER+) human breast cancer cell lines MCF-7 and Zr-75-1 are subjected to in vivo screening. The Glide XP docking was performed for designed scaffold to optimize its structural requirement for ER-α inhibition.

Monoamine Oxidase Inhibitory Activity: Methyl- versus Chlorochalcone Derivatives

Numerous studies have shown that chalcones are promising scaffolds for the development of new monoamine oxidase-B (MAO-B) inhibitors. As a continuation of our ongoing research into the development of reversible human MAO-B (hMAO-B) inhibitors, two series

Niacin esters of chalcones with tumor-selective properties

Novel series of niacin esters of chalcones 2, 4 and 6 were designed as antineoplastic agents that have the potential to release the chemoprotectant niacin. These enones are cytotoxic to human CD4 +T-lymphocyte Molt 4/C8 and CEM and murine leukemia L1210 cells. Quantitative structure–activity relationship (QSAR) studies of the biodata in series 4 revealed that cytotoxic potency was enhanced by placing electron-repelling groups in one of the aryl rings. The compounds are lethal to HL-60, HSC-2, HSC-3 and HSC-4 neoplasms but less toxic to nonmalignant hepatocyte growth factor, hematopoietic progenitor cell and human periodontal ligament fibroblast cells. Hence, the compounds display tumor-selective toxicity. These chalcones are well tolerated in mice and no overt toxicity was noted. The results establish that in general the compounds in series 2, 4 and 6 have positive characteristics which warrant further studies.

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 and study of antibacterial activity of some 1-phenyl-3-aryl-5-(4- (2-ethanoloxy) phenyl)-1H-pyrazoles

A series of 1-phenyl-3-aryl-5-(4-(2-ethanoloxy) phenyl)-1H-pyrazoles were synthesized from chalcones and studied for their in vitro antibacterial activity. Chalcones i.e., 1-aryl-3-(4-hydroxyphenyl) prop-2-en-1-ones, 1 on reaction with phenyl hydrazine yi