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 
• 1250377-76-4 C₂₄H₂₃FN₄O₂ 
• 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 
• 73110-88-0 4'-(N,N-dimethylamino)flavan 
• 1552-96-1 p-dimethylaminocinnamic acid 
• 101442-35-7 4'-(N,N-dimethylamino)-3-hydroxyflavone 
• 1210039-56-7 1-[3-{4-(dimethylamino)phenyl}-1-(2-hydroxyphenyl)allylidene]-4-(4-fluorophenyl)semicarbazide 
• 1210039-46-5 1-[3-{4-(dimethylamino)phenyl}-1-(2-hydroxyphenyl)allylidene]-4-(4-bromophenyl)semicarbazide 
• 1332500-86-3 C₁₈H₁₈N₂O₂ 
• 81136-35-8 Acetic acid 2-[5-(4-dimethylamino-phenyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrazol-3-yl]-phenyl ester 
• 81136-34-7 3-(2-hydroxyphenyl)-5-(4-dimethylaminophenyl)-4,5-dihydro-1-toluenesulphonylpyrazole 

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.

A fluorescence turn-on probe for hydrogen sulfide and biothiols based on PET & TICT and its imaging in HeLa cells

In this paper, a photoinduced electron transfer (PET)& twisted intramolecular charge transfer (TICT)-based fluorescent probe (1) for detecting biothiols (GSH/Cys/Hcy) and hydrogen sulfide with fluorescence turn on was developed. The probe could recognize

Fluorogenic recognition of Zn2+, Cd2+ by a new Pyrazoline-based Multi-Analyte chemosensor and its application in live cell imaging

A novel multi-response pyrazoline-based fluorescent probe 1 was designed and synthesized with a very simple molecular structure, which exhibited high sensitivity for detecting Zn2+ and Cd2+ in ethanol aqueous solution state based on

A simple chalcone molecular rotor for specific fluorescence imaging of mitochondrial viscosity changes in living cells

Mitochondrial viscosity is related to numerous physiological processes such as solute diffusion, enzyme catalysis, protein folding, translocation, and conformation change. It is significant to evaluate and monitor the mitochondrial viscosity changes in li

Experimental and theoretical insights into the photophysical and electrochemical properties of flavone-based hydrazones

A small library of flavone-based hydrazones has been designed, synthesized and characterized. In this context, thirteen flavone hydrazones (3a-3 m) were synthesized by the acid-catalyzed condensation of flavone with 2,4-dinitrophenylhydrazine (2,4-DNPH) and characterized by different spectral techniques (IR, UV–Vis, NMR and mass spectrometry). The electrochemical, photophysical and theoretical investigations of such type of compounds are hitherto unknown. The electrochemical behavior of these hydrazones at a platinum electrode has been analyzed by cyclic voltammetry (CV) and was investigated at 200, 100 and 40 mVs?1 in acetonitrile (CH3CN). These hydrazones showed a quasi-reversible redox reaction. The oxidation–reduction reactive sites of these derivatives were located via geometry optimization using density functional theory (DFT) at the B3LYP/3–21 g in the Guassian-09 level of theory. Moreover, the target compounds exhibited interesting fluorescent properties. Owing to their excellent photophysical and redox results, a detailed structure-property relationship was established to assess the substituents impact and their position on the physicochemical and electronic properties. All the experimental results were in accordance with the computational studies.

Glycolytic inhibition and antidiabetic activity on synthesized flavanone scaffolds with computer aided drug designing tools

Background: Diabetes mellitus is a challengeable metabolic disorder that leads to a group of complications when the HbA1c level is not maintained. Most of the existing drugs avail-able in the market in long-term use may lead to serious adverse effects. He

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