19275-68-4

Usage

InChI:InChI=1/C16H12O3/c1-10-6-8-11(9-7-10)16-15(18)14(17)12-4-2-3-5-13(12)19-16/h2-9,18H,1H3

Upstream product

• 134051-31-3 1a,7a-Dihydro-1a-(4-methylphenyl)-7H-oxireno<1>benzopyran-7-one 
• 86628-44-6 3-nitro-2-(4-methylphenyl)-2H-chromene 
• 155723-53-8 2,4,4-Trimethoxy-2-p-tolyl-chroman-3-ol 
• 41255-30-5 4'-methylflavone 
• 4010-26-8 2-acetylphenyl-4-methyl benzoate 
• 118-93-4 o-hydroxyacetophenone 
• 874-60-2 4-methyl-benzoyl chloride 
• 5067-22-1 1-(2-hydroxyphenyl)-3-(4-methylphenyl)propane-1,3-dione 
• 89839-87-2 2-(4-methylphenyl)-2,3-dihydro-4H-chromen-4-one 
• 13400-26-5 3-hydroxychromen-4-one 
• 637-60-5 p-tolylhydrazine hydrochloride 
• 104-87-0 4-methyl-benzaldehyde 
• 34000-27-6 1-(2-hydroxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one 
• 1233689-66-1 3-hydroxy-2-p-tolylchroman-4-one 

Downstream Products

• 21615-75-8 3-(4-tolyl)-isobenzofuranone 
• 78396-41-5 3-Hydroxy-3-p-tolyl-indan-1,2-dione 
• 263154-44-5 3-(methoxymethyl)oxy-4'-methylflavone 
• 263153-73-7 3-(methoxymethyl)oxy-4'-(bromomethyl)flavone 
• 157077-02-6 Co(C₂H₄(NCHC₆H₄O)2)(C₉H₄O₃C₆H₄CH₃) 
• 241128-49-4 Cu(PPh₃)2(4'-methylflavonolate) 
• 359643-69-9 Zn(II) 4'-methylflavonolate (3,3'-iminobis(N,N-dimethylpropylamine)) perchlorate 
• 255719-45-0 Cu(C₁₆H₁₁O₃)2 
• 1376044-10-8 [chlorido{3-(oxo-κO)-2-(4-methylphenyl)-chromen-4(1H)-onato-κO}(η⁶-p-cymene)ruthenium(II)] 

Relevant academic research and scientific papers

An ESIPT Probe for the Ratiometric Imaging of Peroxynitrite Facilitated by Binding to Aβ-Aggregates

A series of 3-hydroxyflavone (3-HF) ESIPT (excited-state intramolecular proton transfer) boronate-based fluorescent probes have been developed for the detection of peroxynitrite (ONOO-). The dyes are environmentally sensitive, and each probe exhibited a ratiometric response toward ONOO-in a micellar environment. The probes were used to image different aggregation states of amyloid-β (Aβ) in the presence of ONOO-. The3-HF-OMeprobe was found to produce a ratiometric response toward ONOO-when bound to Aβ aggregates, resulting in a novel host-guest ensemble, which adds insight into the development of other ESIPT-based probes for the simultaneous sensing of fibrous proteins/peptides and environmental ROS/RNS.

The three-component photoinitiating systems based on flavonol sulfonate and application in 3D printing

Three-dimensional (3D) printed photocurable shape-shifting polymers based on a three-component photoinitiated system (PIS) (flavonol sulfonate/triethanolamine/iodonium salt) were studied. The flavonol sulfonate (3HF–F) with charge transfer ability and long-wavelength absorption was designed and prepared using the Algar–Flynn–Oyamada method which is an important component of the oxidation–reduction PIS initiating the polymerization of polyethylene glycol (600) diacrylate (PEGDA) under 405 nm LED. For light absorption (active absorber) and electron/proton transfer, the three-component PIS has high-function conversion, and short induction period during the photopolymerization of PEGDA. As the same time, 3HF–F could also undergo passive absorption to obtain high-resolution DLP 3D-printed polymers. The printed polymers could be reversibly modified by means of hydrophilic and thermal responses caused by the stimuli-responsiveness of the polymer chains to activate the shifting of shape.

Water stable fluorescent organotin(iv) compounds: aggregation induced emission enhancement and recognition of lead ions in an aqueous system

Herein, synthesis, spectroscopic studies, single-crystal X-ray diffraction, aggregation-induced emission enhancement (AIEE) and sensing application of water-stable organotin(iv) compounds (4a-6aand4b-6b) obtained from 3-hydroxy-4H-chromen-4-one ligands are reported. All the synthesized organotin(iv) compounds were characterized using elemental analysis, FT-IR spectroscopy, multi-nuclei NMR (1H,13C, and119Sn) spectroscopy, UV-VIS, fluorescence spectroscopy, mass spectrometry, and single-crystal X-ray diffraction. The119Sn NMR signal of compounds in the range ofδ?144.92 to ?190.68 ppm indicated the formation of hexacoordinated organotin species. The spectroscopic and single-crystal X-ray diffraction studies confirmed the formation of [L2SnR2] type compounds (where L is the bidentate ligand and R is an alkyl group) with a ‘skew-trapezoidal bipyramidal’ geometry. Furthermore, DFT calculations of compound4bbased on the DGDZVP basis set fully supported the stability of the structure where two short bonds Sn-O(C-O)acquire thecisposition rather than thetransposition. Single-crystal X-ray diffraction analysis of the crystals grown in the presence of water confirmed the stability of4ain water. Moreover, the water stability of a test compound4awas established by119Sn NMR data and spectrofluorimetric data. The spectrofluorimetric scan at different time intervals revealed the stability and constant emission response up to 24 h. The compounds were found to be fluorescent and exhibited aggregation-induced emission enhancement in MeOH/H2O mixtures, which was confirmed by HRTEM analysis. The test compound4ashowed selective spectrofluorimetric recognition of Pb2+ions in an aqueous medium by displaying an enhanced emission signal at 478 nm and enabled detection up to 22.66 μM. A mechanism of interaction is also proposed by spectroscopic experiments, spectrofluorimetric experiments and computational studies.

Exploring 3-Benzyloxyflavones as new lead cholinesterase inhibitors: synthesis, structure–activity relationship and molecular modelling simulations

In this protocol, a series of 3-benzyloxyflavone derivatives have been designed, synthesized, characterized and investigated in?vitro as cholinesterase inhibitors. The findings showed that all the synthesized target compounds (1–10) are potent dual inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes with varying IC50 values. In comparison, they are more active against AChE than BChE. Remarkably, amongst the series, the compound 2 was identified as the most active inhibitor of both AChE (IC50 = 0.05 ± 0.01 μM) and BChE (IC50 = 0.09 ± 0.02 μM) relative to the standard Donepezil (IC50 = 0.09 ± 0.01 for AChE and 0.13 ± 0.04 μM for BChE). Moreover, the derivatives 5 (IC50 = 0.07 ± 0.02 μM) and 10 (0.08 ± 0.02 μM) exhibited the highest selective inhibition against AChE as compared to the standard. Preliminary structure-activity relationship was established and thus found that cholinesterase inhibitory activities of these compounds are highly dependent on the nature and position of various substituents on Ring-B of the 3-Benzyloxyflavone scaffolds. In order to find out the nature of binding interactions of the compounds and active sites of the enzymes, molecular docking studies were carried out. (Figure presented.) HIGHLIGHTS 3-benzyloxyflavone analogues were designed, synthesized and characterized. The target molecules (1–10) were evaluated for their inhibitory potential against AChE and BChE inhibitory activities. Limited structure-activity relationship was developed based on the different substituent patterns on aryl part. Molecular docking studies were conducted to correlate the in?vitro results and to identify possible mode of interactions at the active pocket site of the enzyme. Communicated by Ramaswamy H. Sarma.

Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies

To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened for in?vitro against mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis, 1H-, 13C-NMR) and mass spectrometry (EI-MS). The structure of compound 15 was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibiotics i.e. Cefixime and Clotrimazole. Amongst the series, the compounds 2, 4, 5, 6, 7, 10, 11, 14 and 22 exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound 2 (IC50 = 0.280 ± 0.010 μg/ml) was found almost sixfold and derivative 5 (IC50 = 0.230 ± 0.020 μg/ml) about sevenfold more active as compared to standard Kojic acid (IC50 =1.79 ± 0.6 μg/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma.

Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone

A novel synthetic method for flavonol from 2′-hydroxyl acetophenone and benzaldehyde promoted by pyrrolidine under an aerobic condition in water is established. This protocol was supported by efficient synthesis of 44 common examples and three natural products. The α, β-unsaturated iminium ion (enimine ion E) was proved to be the key intermediate in the reaction. H218O and 18O2 isotope tracking experiments demonstrated that both water and the aerobic atmosphere were necessary to ensure the transformation. The selectivity for flavonol or aurone was originated from solvent-triggered intermediates, which were determined by UV-visible spectra from isolated enimine. The phenol-iminium E-A is dominant in water and the ketoenamine intermediate E-B is prevalent in acetonitrile. In the presence of pyrrolidine and oxygen, E-A leads to flavonol through E-I, a zwitterionic-like phenoloxyl-iminium ion, following the key steps of cyclization and a [2 + 2] oxidation; E-B proceeds through path II, a radical process induced by photolysis of E-B with both pyrrolidine and oxygen, to afford aurone. Preliminary mechanistic studies are reported.

Flavonol dyes with different substituents in photopolymerization

To further expand the applications of flavonol dyes (3HFs) in photopolymerization, six flavonol dyes with different substituents were prepared by using the Algar–Flynn–Oyamada method. The steady-state photolysis and fluorescence quenching of 3HFs under the 385 nm LED light source showed that the proton transfer reaction preceded the charge transfer reaction between 3HFs and triethanolamine (TEOA) or iodonium salts (ONI), and groups with different electron properties could affect the photochemistry of 3HFs. The influence of substituents on the free radical polymerization efficiencies of 3HFs/TEOA and 3HFs/ONI was evaluated. Results showed that charge transfer occurred in the oxidation or reduction processes between 3HFs and TEOA or ONI. The possible mechanism was speculated, and the thermal feasibility of charge transfer between 3HFs and TEOA or ONI was calculated on the basis of the free energy changes of photoinduced electron transfer.

Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis

Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.

Design, synthesis, and biological evaluation of Helicobacter pylori inosine 5′-monophosphate dehydrogenase (HpIMPDH) inhibitors

Inosine 5′-monophosphate dehydrogenase (IMPDH) catalyzes a crucial step in the biosynthesis of guanine nucleotides. Being a validated target for immunosuppressive, antiviral, and anticancer drug development, lately it has been exploited as a promising target for antimicrobial therapy. Extending our previous work on Mycobacterium tuberculosis IMPDH, GuaB2, inhibitor development, we screened a set of 23 new chemical entities (NCEs) with substituted flavone (Series 1) and 1,2,3-triazole (Series 2) core structures for their in vitro Helicobacter pylori IMPDH (HpIMPDH) and human IMPDH2 (hIMPDH2) inhibitory activities. All the NCEs possessed acceptable molecular, physicochemical, and toxicity property profiles. The ranges for HpIMPDH and hIMPDH2 inhibition were 9–99.9% and 16–57%, respectively, at 10 μM concentration. The most potent HpIMPDH inhibitor, 25c, exhibited IC50 value of 1.27 μM with no hIMPDH2 inhibitory activity. The moderately potent, structurally novel hit molecule, 25c, may serve as a lead for further design and development of highly potent HpIMPDH inhibitors.

Hydroxyl directed: C -arylation: Synthesis of 3-hydroxyflavones and 2-phenyl-3-hydroxy pyran-4-ones under transition-metal free conditions

An efficient, transition-metal free and direct C-arylation of 3-hydroxychromone moieties in the presence of a base, air as an oxidant and arylhydrazines as arylating agents to furnish highly biologically active flavonols or 3-hydroxyflavones has been developed. We have further extended our methodology for the C-arylation of the 5-hydroxy pyran-4-one moiety. The role of the free hydroxyl group towards C-arylation has been delineated.