65786-13-2

Usage

Uses

Used in Pharmaceutical Industry:
(2E)-3-[4-(Dimethylamino)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one is used as an intermediate in the synthesis of pharmaceuticals for its potential therapeutic properties. It has been investigated for its antioxidant and anti-inflammatory effects, which can contribute to the development of new medications.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, (2E)-3-[4-(Dimethylamino)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one is used as a key component in the synthesis of various organic compounds, highlighting its versatility and importance in chemical research and development.
Used in Anticancer Research:
(2E)-3-[4-(Dimethylamino)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one is being studied for its potential use in the treatment of cancer due to its therapeutic properties. Its role in this area is still under investigation, but the compound holds promise for future cancer therapies.
Used in Diabetes Treatment Research:
Additionally, (2E)-3-[4-(Dimethylamino)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one has been explored for its potential application in the treatment of diabetes. The research into its use for this condition is ongoing, and it may lead to advancements in diabetes management and treatment options.

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 77038-22-3 2-[4-(dimethylamino)phenyl]-2,3-dihydro-4H-chromen-4-one 

Downstream Products

• 101783-04-4 [4-(4-dimethylamino-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-(2-hydroxy-phenyl)-ketone 
• 81136-30-3 3-(2-hydroxyphenyl)-5-(4-dimethylaminophenyl)-4,5-dihydro-1H-pyrazole 
• 81136-34-7 3-(2-hydroxyphenyl)-5-(4-dimethylaminophenyl)-4,5-dihydro-1-toluenesulphonylpyrazole 
• 81136-35-8 Acetic acid 2-[5-(4-dimethylamino-phenyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrazol-3-yl]-phenyl ester 
• 1250377-76-4 C₂₄H₂₃FN₄O₂ 
• 1332500-86-3 C₁₈H₁₈N₂O₂ 
• 77038-22-3 2-[4-(dimethylamino)phenyl]-2,3-dihydro-4H-chromen-4-one 
• 112980-33-3 Z-2-[(4-N,N-dimethylaminophenyl)methylene]benzo[b]furan-3-one 
• 50287-25-7 2-(4-(dimethylamino) phenyl)-4H-chromen-4-one 
• 70170-84-2 NL-31 

Relevant academic research and scientific papers

Microwave Assisted Synthesis, Optical Properties and Physicochemical Investigations on the Powerful Fluorophore: Donor (D) -π-Acceptor (A) Chalcone

(2E)-3-[4-(dimethylamino)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one (DPHP) was synthesized by the reaction 4(dimethylamino) benzaldehyde with 1-(2-hydroxyphenyl) ethanone under microwave irradiation. Structure of DPHP was conformed by 1H and s

2′-hydroxy-4″-dimethylamino-chalcone

The title compound, 3-[4-(dimethylamino)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one, C17H17NO2, is a chalcone derivative substituted by 2′-hydroxyl and 4″-dimethylamino groups. The crystal structure indicates that the anili

Evaluation of Novel Chalcone Oximes as Inhibitors of Tyrosinase and Melanin Formation in B16 Cells

A series of hydroxy-substituted chalcone oxime derivatives were synthesized. These compounds were then evaluated for their inhibitory activities on tyrosinase and melanogenesis in murine B16F10 melanoma cells. The structures of the synthesized compounds were confirmed by 1H NMR, 13C NMR, FTIR, and HRMS. Two of the compounds exhibited much higher tyrosinase inhibitory activities (IC50 values of 4.77 and 7.89 μM, respectively) than the positive control, kojic acid (IC50: 22.25 μM). Kinetic studies revealed them to act as competitive tyrosinase inhibitors with their Ki values of 5.25 and 8.33 μM, respectively. Both the compounds inhibited melanin production and tyrosinase activity in B16 cells. Docking results confirmed that the active inhibitors strongly interacted with the mushroom tyrosinase residues.

Flavone-based hydrazones as new tyrosinase inhibitors: Synthetic imines with emerging biological potential, SAR, molecular docking and drug-likeness studies

Targeting tyrosinase (TYR), a key enzyme responsible for melanogenesis disorders, is a well-known approach utilized for the development of melanogenesis inhibitor. A variety of dermatological disorders and microbial skin infections can cause hyperpigmentation. Hence, exploring new scaffolds for the treatment of melanogenesis disease is an inspiring goal. In this context, a series of varyingly substituted flavone-based hydrazones have been designed, synthesized and characterized successfully. The present study describes the discovery of novel mushroom tyrosinase inhibitors (TIs) for treating hyperpigmentation. In due course, flavone scaffold has been incorporated into the novel chemotypes that exhibit in vitro inhibitory effects against mushroom tyrosinase for the purpose of discovering anti‐melanogenic agents. Biological investigations of prepared analogs herein demonstrated moderate to excellent activity against most of the fungal-bacterial strains and their activity is comparable to those of commercially available antibiotics i.e., Ciprofloxacin and Ketoconazole. Based on in vitro tyrosinase inhibitory assay, some compounds exhibited potent inhibition particularly, 3g (IC50 = 1.40 ± 0.16 μM), 3j (IC50 = 0.95 ± 0.07 μM), 3o (IC50 = 1.13 ± 0.11 μM), and 3q (IC50 = 1.01 ± 0.1 μM) showed best inhibition i.e., 0.7, 0.5, 0.6 and 0.5 folds, respectively, than kojic acid (IC50 = 1.79 ± 0.6 μM). Lineweaver-Burk plots demonstrated that the most potential derivative 3j tyrosinase inhibition proceeds via non-competitive pathway and the Michaelis-Menton constant (Km) value is 0.0265. Molecular modeling was performed for all tested analogs (3a–3q) using a model of mushroom tyrosinase to find crucial binding modes liable for inhibitory activity. The SARs were preliminarily examined, and the docking study revealed that analogs 3j, 3o and 3p had a strong binding association to tyrosinase (2Y9X). Furthermore, a drug-likeness study was employed and confirmed the favorable activity of the new analogs as a new anti-tyrosinase agent.

Crystal-packing modes determine the solid-state ESIPT fluorescence in highly dipolar 2′-hydroxychalcones

This work describes the systematic study of the structure-luminescence relationship of 15 hydroxy-chalcones directly in the crystal state. Chalcones are easily assembled at the gram scale allowing for efficient variation of their substitution motifs. Our molecule variants combine two modes of fluorescence generation, ESIPT and ICT, both known for their potential to achieve significant quantum yields even with emission in the red to near infrared, a region preferred for technologies as diverse as optoelectronics and chemical sensing. Quantum yields as high as 48% (at 665 nm) and emission wavelengths in the deep red region (710 nm, 5%) were achieved with variants equipped with a strained amino substituent in the donor portion (azetidinyl). Systematic XRD analysis of large monocrystals allowed for the identification of the subtle interplay of several inter- and intra-molecular parameters in achieving such performances, be it intramolecular planarity, non-classical H-bonds, and stacking modes.

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.

Structural and spectroscopic analysis and evaluation of cytotoxic activity of 2-hydroxychalcones against human cancer cell lines

Chalcones and their derivatives exhibit a broad spectrum of pharmacological activities, including antiproliferative activities. Accordingly, they are deemed robust anticancer candidates for cytotoxicity assays. Herein, we synthesized and characterized fou

Sensor array system for discrimination and detection for reactive chemical species comprising fluorescence compounds

The present invention relates to a sensor array system comprising a fluorescent compound for discrimination and detection of active species. 2 Or more compounds according to one aspect, hydrates, solvates or salts thereof, compositions for detecting active species including the same, sensor arrays, or methods of detecting active species using the same are capable of selectively distinguishing various active species. The present invention relates to a composition for detecting an active species, a method for detecting an active species, and a method for detecting an active species.

AIE + ESIPT activity-based NIR Cu2+sensor with dye participated binding strategy

A novel activity-based Cu2+fluorescent probe featuring multidentate binding sites was synthesized. It functions through chelation with Cu2+, which in turn specifically triggers hydrolysis of the probe to release a near-infrared emiss

A Solvatochromic Fluorescent Probe Reveals Polarity Heterogeneity upon Protein Aggregation in Cells

We report a crystallization-induced emission fluorophore to quantitatively interrogate the polarity of aggregated proteins. This solvatochromic probe, namely “AggRetina” probe, inherently binds to aggregated proteins and exhibits both a polarity-dependent fluorescence emission wavelength shift and a viscosity-dependent fluorescence intensity increase. Regulation of its polarity sensitivity was achieved by extending the conjugation length. Different proteins bear diverse polarity upon aggregation, leading to different resistance to proteolysis. Polarity primarily decreases during protein misfolding but viscosity mainly increases upon the formation of insoluble aggregates. We quantified the polarity of aggregated protein-of-interest in live cells via HaloTag bioorthogonal labeling, revealing polarity heterogeneity within cellular aggregates. The enriched micro-environment details inside misfolded and aggregated proteins may correlate to their bio-chemical properties and pathogenicity.