6342-97-8

Usage

InChI:InChI=1/C17H17NO2/c1-18(2)14-10-7-13(8-11-14)9-12-17(20)15-5-3-4-6-16(15)19/h3-12,19H,1-2H3/b12-9+

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 100-10-7 4-dimethylamino-benzaldehyde 

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 
• 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 
• 1606142-38-4 4-(2-hydroxyphenyl)-2-(4-(N,N-dimethylamino)phenyl)-2,3-dihydro-1,5-benzothiazepine 
• 70170-84-2 NL-31 

Relevant academic research and scientific papers

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

An ESIPT coupled AIE fluorescent probe for biothiols detection and imaging based on a chalcone fluorophore

Biothiols are closely related to numerous physiological and pathological processes in living organisms and cells. Fluorescent probes are powerful tools for sensitive detection and imaging of biothiols in biological samples. In this work, we developed a no

NIR luminescence for the detection of latent fingerprints based on ESIPT and AIE processes

In this paper, a facile near infrared (NIR, 650-900 nm) probe 4-dimethylamino-2′-hydroxychalcone (NIR-LP) based on the excited state intramolecular proton transfer (ESIPT)-aggregation induced emission (AIE) processes for the detection of the latent finger

An ultrasensitive rapid-response fluorescent probe for highly selective detection of HSA

A fluorescent probe HCAB based on twisted intramolecular charge transfer (TICT) mechanism has been designed and synthesized by introducing benzoyl moiety to 4-dimethylamino-2′-hydroxychalcone. HCAB showed excellent selectivity towards human serum albumin

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

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

Synthesis and kinetic study for the interconversion process of some 2'-hydroxychalcones to their corresponding flavanones

In this work, five substituted2'-Hydroxychalconeswere prepared using Claisen - Schmidt condensation and used as a synthone for substituted flavanones via base catalyzed isomerization process. The latter process has been studied kinetically using HPLC technique in (8:2) (CH3CN:CH3OH) medium at different temperatures (298 K - 318 K). The obtained results were inconsonance with a four-step mechanism which considered the existence of phenoxide ion as the key intermediate. The reaction was achieved as a pseudo first order reaction in which the rate of the studied compounds followed the sequence 1>2>3>4>5, and the activation energy had the same sequence for these compounds. The reaction rate was affected by the electronic behavior of the different substituents at ring B since they played an important role in the stability of the intermediate that led to the final product.