19152-36-4

Usage

Uses

Used in Pharmaceutical Industry:
3,4-DIMETHOXY-2'-HYDROXYCHALCONE is used as a key intermediate in the synthesis of new flavanoid and chalcone derivatives, which possess antimicrobial properties. These derivatives are valuable in the development of novel antimicrobial agents, addressing the growing need for new treatments against drug-resistant infections.
Used in Green Chemistry:
3,4-DIMETHOXY-2'-HYDROXYCHALCONE is used as a building block for the synthesis of new flavanoid and chalcone derivatives through a green chemistry approach. This method focuses on reducing the environmental impact of chemical processes, making it a sustainable and eco-friendly option for the development of new antimicrobial agents.

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 39856-08-1 3,4-dimethoxy-cinnamoyl chloride 
• 108-95-2 phenol 

Downstream Products

• 81136-28-9 3-(2-hydroxyphenyl)-5-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazole 
• 88701-90-0 4-[(E)-2-(3,4-Dimethoxy-phenyl)-vinyl]-benzo[e][1,2,3]oxathiazine 2,2-dioxide 
• 6889-80-1 2-(3,4-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one 
• 105166-58-3 2-Hydroxy-benzoic acid [2-(3,4-dimethoxy-phenyl)-chroman-(4E)-ylidene]-hydrazide 
• 3772-03-0 2'-Benzyloxy-3,4-dimethoxy-chalkon 
• 4143-62-8 3',4'-dimethoxyflavone 
• 6344-21-4 3',4'-dimethoxyflavanone 
• 81136-33-6 3-(2-hydroxyphenyl)-5-(3,4-dimethoxyphenyl)-4,5-dihydro-1-toluenesulphonylpyrazole 
• 81136-29-0 Acetic acid 2-[5-(3,4-dimethoxy-phenyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrazol-3-yl]-phenyl ester 
• 134720-25-5 2-(3,4-dimethoxyphenyl)-4-(2-hydroxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepine 
• 117198-53-5 3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)-2-propen-1-one palladium 
• 117198-54-6 3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)-2-propen-1-one platinum (II) 
• 189073-42-5 RuCl₂(C₆H₄(O)C(O)CHCHC₆H₃(OCH₃)2)(P(C₆H₅)3)2 
• 189073-43-6 RuCl₂(C₆H₄(O)C(O)CHCHC₆H₃(OCH₃)2)(As(C₆H₅)3)2 

Relevant academic research and scientific papers

Crystal structures, Hirshfeld surface analysis and PIXEL calculations of four (E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one derivatives, containing methoxy substituents. The importance of π interactions

A detailed structural analysis has been carried out on four chalcone (E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one derivatives, having a varying number of methoxy substituents, namely (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one, (1),

Photophysical investigation of (D-π-A) DMHP dye: Dipole moments, photochemical quantum yield and fluorescence quantum yield, by solvatochromic shift methods and DFT studies

(2E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (DMHP) was synthesized by the reaction of 3,4-dimethoxy benzaldehyde with 1-(2-hydroxyphenyl) ethanone under microwave irradiation. The structure of DMHP was established experimentally by EI-

A new class of flavonol-based anti-prostate cancer agents: Design, synthesis, and evaluation in cell models

Flavonoids are a large class of polyphenolic compounds ubiquitously distributed in dietary plants with an array of biological activities. Flavonols are a major sub-class of flavonoids featuring a hydroxyl group at C-3. Certain natural flavonols, such as q

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.

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

A novel one-pot synthesis of flavones

In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.

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.

Synthesis and antibacterial activity of chalcone derivatives containing thioether triazole

The infection of Xanthomonas oryzae pv. Oryzae (Xoo), Ralstonia solanacearum (Rs), and Xanthomonas axonopodis pv. Citri (Xac) has become a major problem in agricultural production. In this study, a series of novel chalcone derivatives containing thioether triazoles were designed and synthesized. The structures of the novel compounds were systematically characterized via 1H-NMR, 13C-NMR, and HRMS. Moreover, the antibacterial activity results showed that E10, E11, E15, and E16 have adequate antibacterial activities against Xoo, Rs, and Xac. Among the different compounds, E15 exhibited remarkable inhibitory effect against Xac with an EC50 of 9.1 μg.mL-1, which was better than that of commercial agent bismerthiazol (54.9 μg.mL-1). In addition, the possible antibacterial mechanism of the target compound E15 against Xac was studied via scanning electron microscopy (SEM).

Multi-step synthesis, photophysical and physicochemical investigation of novel pyrazoline a heterocyclic D- π -A chromophore as a fluorescent chemosensor for the detection of Fe3+ metal ion

The title compound has been 2-(1-(benzo[d]thiazol-2-yl)-5-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenol (BTDP) synthesized by reaction of (E)-3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one (DMPO) with 2-Hydrazinylbenzo[d]thiazole. DMPO was synthesized by the reaction of 1-(2 hydroxyphenyl)ethan-1-one with 3,4-dimethoxybenzaldehyde. Structure of compound has been confirmed by the elemental analysis and spectroscopic techniques (FT-IR, 1H NMR and 13C NMR). Photophysical properties of the BTDP such as absorption, emission, stokes shift, transition dipole moments and fluorescence quantum yield have been studied in various solvents of different polarity and chromophore demonstrated positive solvatochromism. The chromophore undergoes micellization in two different micelles and its can be used as probe to determine the critical micelle concentration of surfactant such as CTAB and SDS. In addition, Pyrazoline derivative used as fluorescent chemosensor for metal ion selectively based on fluorometric detraction and pyrazoline displayed as on-off fluorescence chemosensor for the determination of Fe3+ ion in solution. Hildebrand, Stern-Volmer and job's plot method has described quenching behavior of chromophore with Fe3+ ion.

Bismuth(III) Flavonolates: The Impact of Structural Diversity on Antibacterial Activity, Mammalian Cell Viability and Cellular Uptake

A series of homoleptic and heteroleptic bismuth(III) flavonolate complexes derived from six flavonols of varying substitution have been synthesised and structurally characterised. The complexes were evaluated for antibacterial activity towards several problematic Gram-positive (Staphylococcus aureus, methicillin-resistant Staphylococcus aureus (MRSA), and vancomycin-resistant Enterococcus (VRE)) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria. The cell viability of COS-7 (monkey kidney) cells treated with the bismuth flavonolates was also studied to determine the effect of the complexes on mammalian cells. The heteroleptic complexes [BiPh(L)2] (in which L=flavonolate) showed good antibacterial activity towards all of the bacteria but reduced COS-7 cell viability in a concentration-dependent manner. The homoleptic complexes [Bi(L)3] exhibited activity towards the Gram-positive bacteria and showed low toxicity towards the mammalian cell line. Bismuth uptake studies in VRE and COS-7 cells treated with the bismuth flavonolate complexes indicated that Bi accumulation is influenced by both the substitution of the flavonolate ligands and the degree of substitution at the bismuth centre.