36768-48-6

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
(E)-1-(5-chloro-2-hydroxy-phenyl)-3-(4-chlorophenyl)prop-2-en-1-one is used as a chemical intermediate for the development of new drugs. Its unique structure, which includes chloro and hydroxy groups in the phenyl rings, makes it a promising candidate for the creation of novel pharmaceutical compounds with potential therapeutic applications.
Used in Drug Discovery and Development:
In the field of drug discovery and development, (E)-1-(5-chloro-2-hydroxy-phenyl)-3-(4-chlorophenyl)prop-2-en-1-one is used as a key compound for exploring its potential in creating new drugs. (E)-1-(5-chloro-2-hydroxy-phenyl)-3-(4-chlorophenyl)prop-2-en-1-one's enone structure and the presence of functional groups in the phenyl rings make it an attractive starting point for designing and synthesizing new molecules with specific biological activities.
Used in Research and Development of Chemical Compounds:
(E)-1-(5-chloro-2-hydroxy-phenyl)-3-(4-chlorophenyl)prop-2-en-1-one is also used in the research and development of chemical compounds, particularly in the context of understanding its chemical reactivity and potential applications in various chemical processes. (E)-1-(5-chloro-2-hydroxy-phenyl)-3-(4-chlorophenyl)prop-2-en-1-one's unique structure allows researchers to investigate its interactions with other molecules and its potential use in the synthesis of new materials or compounds with specific properties.

Upstream product

• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 139006-35-2 (2S,3R)-6-Chloro-2-(4-chloro-phenyl)-4,4-dimethoxy-chroman-3-ol 
• 111391-55-0 6-chloro-2-(4-chlorophenyl)-3-hydroxy-4H-chromen-4-one 
• 139006-43-2 (2R,3S)-6-Chloro-2-(4-chloro-phenyl)-3-hydroxy-chroman-4-one 
• 73110-56-2 4',6-dichloroflavan 
• 36768-56-6 6-chloro-2-(4-chlorophenyl)-4H-chromen-4-one 
• 6336-05-6 6,4'-dichloroflavanone 
• 1363408-67-6 C₁₅H₁₀Br₂Cl₂O₂ 
• 1363408-72-3 C₂₁H₁₄Cl₂N₂O 
• 73110-92-6 6-chloro-2-(4-chlorophenyl)-2H-chromene 
• 86882-42-0 4-Chloro-2-[2-(4-chloro-phenyl)-1,1-dioxo-2,3-dihydro-1H-1λ⁶-benzo[b][1,4]thiazepin-4-yl]-phenol 
• 86882-10-2 4-Chloro-2-[2-(4-chloro-phenyl)-2,3-dihydro-benzo[b][1,4]thiazepin-4-yl]-phenol 
• 111391-74-3 6-Chloro-2-(4-chloro-phenyl)-3-methoxy-chromen-4-one 
• 78778-10-6 5-(5-chloro-2-hydroxy-phenyl)-7-(4-chloro-phenyl)-7,8-dihydro-3-methyl-6H-isoxazolo[4,5-b]azepine 

Relevant academic research and scientific papers

Multitarget 2′-hydroxychalcones as potential drugs for the treatment of neurodegenerative disorders and their comorbidities

The complex nature of neurodegenerative diseases (NDDs), such as Alzheimer's disease (AD) and Parkinson's disease (PD) calls for multidirectional treatment. Restoring neurotransmitter levels by combined inhibition of cholinesterases (ChEs) and monoamine oxidases (MAOs, MAO-A and MAO-B), in conjunction with strategies to counteract amyloid β (Aβ) aggregation, may constitute a therapeutically strong multi-target approach for the treatment of NDDs. Chalcones are a subgroup of flavonoids with a broad spectrum of biological activity. We report here the synthesis of 2′-hydroxychalcones as MAO-A and MAO-B inhibitors. Compounds 5c (IC50 = 0.031 ± 0.001 μM), 5a (IC50 = 0.084 ± 0.003 μM), 2c (IC50 = 0.095 ± 0.019 μM) and 2a (IC50 = 0.111 ± 0.006 μM) were the most potent, selective and reversible inhibitors of human (h)MAO-B isoform. hMAO-B inhibitors 1a, 2a and 5a also inhibited murine MAO-B in vivo in mouse brain homogenates. Molecular modelling rationalised the binding mode of 2′-hydroxychalcones in the active site of hMAO-B. Additionally, several derivatives inhibited murine acetylcholinesterase (mAChE) (IC50 values from 4.37 ± 0.83 μM to 15.17 ± 6.03 μM) and reduced the aggregation propensity of Aβ. Moreover, some derivatives bound to the benzodiazepine binding site (BDZ-bs) of the γ-aminobutyric acid A (GABAA) receptors (1a and 2a with Ki = 4.9 ± 1.1 μM and 5.0 ± 1.1 μM, respectively), and exerted sedative and/or anxiolytic like effects on mice. The biological results reported here on 2′-hydroxychalcones provide an extension to previous studies on chalcone scaffold and show them as a potential treatment strategy for NDDs and their associated comorbidities.

Synthesis, molecular properties, anti-inflammatory and anticancer activities of novel 3-hydroxyflavone derivatives

A new series of 3-hydroxyflavones (1–46) were synthesized according to the Claisen-Schmidt followed by Algar-Flynn-Oyamada reactions (AFO) in one step. The synthesized flavonoids were characterized by 1H NMR, 13C NMR and DCI-HRMS. All the synthesized compounds were tested in vitro for their 15-lipoxygenase inhibitory and cytotoxic activity against the human cell lines HCT-116 (Human colon carcinoma), IGROV-1 and OVCAR-3 (human ovarian carcinoma). It has been found that the derivatives 25, 37 and 45 were the most actives against HCT-116 (IC50 = 8.0, 9.0 and 9.0 μM, respectively) and against IGROV-1 (IC50 = 2.4, 5.0 and 6.0 μM, respectively). The derivatives 14 and 21 exhibited the higher anti-inflammatory activity at 100 μM with PI values of 76.50 and 72.70%, respectively. Molecule description was performed with DFT calculations, the drug likeness and bioactivity scores. The results exhibted that some compounds are in linear correlation with Lipinski's rule of five showing good drug likeness and bioactivity score for drug targets.

Absorption and fluorescent studies of 3-hydroxychromones

The synthesis and spectral studies of variously substituted 3-hydroxychromones have been carried out. A key relationship between the structural motif of synthesized 3-hydroxychromones (3-HCs) and their fluorescent properties was found. The chromones substituted with electron-donating group at 4′-position expressed the red shift of the N and T band and also exhibited the increased fluorescent intensity ratio while the chromones with electron-withdrawing group showed the blue shift of the N and T band. Therefore, these 3-HCs may behave as the possible fluorescent probes.

Synthesis and biological activities of some flavones

Chalcones are synthesized by a base catalyzed Claisen Schmidt condensation reaction and then treated with dimethylsulphoxide in presence of iodine to get flavones. The synthesized compounds were evaluated for their antibacterial activity against Escherichia coli, P. aeruginosa, S. epidermidis and B. subtilis. All the flavones showed moderate to good activity. The structures of these compounds were confirmed by IR, UV, 1H NMR, Mass and elemental analysis.

Synthesis and biological activities of some flavones

Chalcones are synthesized by a base catalyzed Claisen Schmidt condensation reaction and then treated with dimethylsulphoxide in presence of iodine to get flavones. The synthesized compounds were evaluated for their antibacterial activity against Escherichia coilt P. aeruginosa, S. epidermidis and B. subtilis. All the flavones showed moderate to good activity. The structures of these compounds were confirmed by IR, UV, 1H NMR, Mass and elemental analysis.

Synthesis and biological activities of some new quinoxalines

The condensation of 5-chloro-2-hydroxyacetophenone 1 with different substituted aromatic aldehydes in ethanol in presence of strong alkali furnished 1-(2-hydroxy-5-chlorophenyl)-3-aryl propen-1-ones 2a-e. Bromination of compounds 2a-e in acetic acid gave 1-(2-hydroxy-5-chlorophenyl)-3-aryl 2,3-dibromopropan-1-ones 3a-e which upon treatment with o-phenylenediamine in methanol in presence of cone sulphuric acid underwent cyclization and resulted in the formation of quinoxaline derivatives 4ae. Structures of compounds were established on the basis of analytical and spectral studies. Further these compounds were evaluated for their antimicrobial activities and some selected compounds were evaluated for antitubercular activities.

Synthesis of flavanones by use of anhydrous potassium carbonate as an inexpensive, safe, and efficient basic catalyst

Anhydrous potassium carbonate has been utilized as an inexpensive, safe, and efficient basic catalyst for the synthesis of flavanones starting either from 2′-hydroxychalcones or from 2′-hydroxyacetophenones. In both the cases the favored reaction condition was either refluxing in a solvent with added catalyst or microwave irradiation on the catalyst.

Biological evaluation of synthetic analogues of curcumin: Chloro-substituted-20-hydroxychalcones as potential inhibitors of tubulin polymerization and cell proliferation

A series of chloro-substituted-20-hydroxychalcones were prepared and evaluated for their cytotoxic effects against K562 and SK-N-MC human cancer cell lines and as the inhibitors of tubulin polymerization. The 3,50-dichloro- analogue (compound 3) inhibited the assembly of protofilaments with 89% inhibition. Compound 3 was found to be bound to tubulin with a dissociation constant of 3.7 lM and altered far-UV circular dichroism spectrum of tubulin and altered far-UV circular dichroism spectrum of tubulin.

Enantioselective synthesis of chromanes by iridium-catalyzed asymmetric hydrogenation of 4H-chromenes

Iridium complexes of chiral oxazoline-based P,N-ligands proved to be efficient catalysts for the enantioselective hydrogenation of 2-aryl- and 2-alkyl-4H-chromenes. The best results were obtained with a ligand derived from threonine (ThrePHOX), which induced ee values of 95% to >99% in the hydrogenation of 2-methyl-, 2-cyclohexyl- and various 2-aryl-substituted chromenes. Georg Thieme Verlag Stuttgart.

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.