14003-96-4

Usage

Uses

Used in Pharmaceutical Industry:
7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde is used as an inhibitor for blocking substrate access to the active site of IRE1. It selectively inactivates both Xbp1 splicing and IRE1-mediated mRNA degradation, making it a valuable tool in the study and treatment of various diseases related to ER stress and protein misfolding.
Used in Research Applications:
In the field of research, 7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde is used as a selective inhibitor of IRE1α ribonuclease (RNase) activity. It is particularly useful in studying the effects of hypoxia and other ER stress-inducing agents on cellular processes, as well as the role of IRE1α in the production of certain cytokines in T cells.
Used in Cell Biology:
7-hydroxy-4-Methyl-2-oxo-2H-1-Benzopyran-8-carboxaldehyde is used as a research tool to investigate the splicing of the XBP1 mRNA in response to ER stress. This is particularly relevant in the study of pancreatic β-cells and the effects of mutant proinsulin production on cellular function.

Biochem/physiol Actions

Cell permeable: yes

References

1) Cross?et al. (2012),?The molecular basis for selective inhibition of unconventional mRNA splicing by an IRE1-binding small molecule; Proc. Natl. Acad. Sci. USA,?109?E869 2) Cojocari?et al. (2013),?New small molecule inhibitors of UPR activation demonstrate that PERK, but not IRE1α signaling is essential for promoting adaptation and survival to hypoxia;? Radiother. Oncol.,?108?541 3) Kemp?et al. (2013),?The serine-threonine kinase inositol-requiring enzyme 1α (IRE1α) promotes IL-4 production in T helper cells; J. Biol. Chem.,?288?33272 4) Zhang?et al. (2014),?IRE1 inhibition perturbs the unfolded protein response in a pancreatic β-cell line expressing mutant proinsulin, but does not sensitize the cells to apoptosis;? BMC Cell Biol.,?15?29

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 100-97-0 hexamethylenetetramine 
• 86290-39-3 7-<(β-chloroallyl)oxy>-8-formyl-4-methylcoumarin 
• 68-12-2 N,N-dimethyl-formamide 
• 64-19-7 acetic acid 
• 1402244-59-0 1-((7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)methyl)pyrrolidine 1-oxide 
• 3993-57-5 7-allyloxy-4-methyl-2H-chromen-2-one 
• 92646-98-5 7-hydroxy-4-methyl-8-(pyrrolidin-1-ylmethyl)coumarin 
• 108-46-3 recorcinol 
• 141-97-9 ethyl acetoacetate 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 4115-76-8 4,8-dimethyl-7-hydroxycoumarin 
• 2107-77-9 4-methyldaphnetin 
• 1233766-07-8 7-hydroxy-4-methyl-8-([1,1';4',1'']terphenyl-4-ylimino)methyl-2H-1-benzopyran-2-one 
• 111051-68-4 (8-(4'-chlorophenylimino)methyl)-7-hydroxy-4-methyl-2H-1-benzopyran-2-one 
• 1233766-05-6 8-(4'-acetylphenylimino)methyl-7-hydroxy-4-methyl-2H-1-benzopyran-2-one 
• 111051-69-5 7-hydroxy-4-methyl-8-(4-nitrophenylimino)methyl-2H-1-benzopyran-2-one 
• 1403692-30-7 (E)-2-cyano-3-(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)-N-(1-(4-methoxyphenyl)ethyl)acrylamide 
• 1403692-31-8 (E)-2-cyano-3-(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)-N-(1-phenylethyl)acrylamide 
• 1403692-32-9 (E)-N-benzyl-2-cyano-3-(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)acrylamide 
• 1403692-37-4 (E)-2-cyano-N,N-diethyl-3-(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)acrylamide 
• 1403692-42-1 (E)-N-benzhydryl-2-cyano-3-(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)acrylamide 
• 1403692-43-2 (E)-2-cyano-N-(2,4-dimethoxyphenyl)-3-(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)acrylamide 
• 1400695-63-7 C₁₉H₁₁BrO₄ 
• 1417720-40-1 (E)-2-cyano-3-(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)-N-phenylacrylamide 

Relevant academic research and scientific papers

A selective hydrolytic and restructuring approach through a Schiff base design on a coumarin platform for “turn-on” fluorogenic sensing of Zn2+

A new Schiff base, CMD, designed based on a coumarin platform was synthesized and fully characterized through single crystal X-ray diffraction studies. CMD underwent selective Zn2+-triggered hydrolysis in ethanolic medium followed by restructur

A schiff base fluorescent probe for Mg2+ and Zn2+ based on coumarin

A novel fluorescent Schiff base (L) based on coumarin was synthesized and characterized. Addition of Mg2+ and Zn2+ to fluorescent Schiff base in acetonitrile resulted in fluorescence enhancement and little influence was observed for other metal ions. It suggested that fluorescent Schiff base could be used as a potential Mg2+ and Zn2+ fluorescent probe in acetonitrile.

A new coumarin based Schiff base fluorescence probe for zinc ion

Herein, a novel coumarin-based fluorescent probe (FS3) was designed, synthesized, and characterized. It exhibited significant fluorescence quenching in the presence of Zn2+ ions. Just a minor alteration occurred in the fluorescence intensity of

Synthesis, fluorescence properties and F? detection performance of Eu(III) complexes based on the novel coumarin Schiff base derivatives

Three novel coumarin Schiff base derivatives and corresponding Eu(III) complexes were designed and synthesized. The aggregation-induced emission (AIE) property of ligands was studied. The fluorescence properties and electrochemical properties of Eu(III) complexes were investigated by comparing different substituent groups. The ion selectivity and ion detection limits of the [EuL2(NO3)3] ?H2O were also studied. The result indicates that all ligands exhibit the AIE property in CH3CN/H2O solution and emit green fluorescence with the maximum emission wavelength of 552 nm. All complexes show characteristic red fluorescence of Eu(III) and the influence of different substituents on the fluorescence intensity of Eu(III) complexes is ordered: -OCH3 > -H > -NO2, and [EuL2(NO3)3] ?H2O exhibits the strongest fluorescence intensity. The density functional theory (DFT) calculations of the ligands indicate that the introduction of electron-donating groups increases the HOMO energy level and the electron cloud density, which enhance the ability to coordinate with Eu(III) and the fluorescence intensity of the corresponding complex. Besides, the electrochemical properties of Eu(III) complexes indicate that the introduction of electron-donating groups increases the energy gaps (Eg) and the conjugation of the complex, which enhances the fluorescence intensity of the complexes. Ion selectivity experiments show that [EuL2(NO3)3] ?H2O has a specific recognition function for F?, and its response limit is between 1.0 × 10?5 mol·L?1 and 2.2 × 10?5 mol·L?1. Based on the above results, all the ligands and Eu(III) complexes have a promising application in optical materials due to the excellent fluorescence properties. In addition, All Eu(III) complexes also have a potential application prospects in the field of fluoride ion detection.

A new strategy for synthesis of 9-benzoyl-4-methylpyrano[2,3-f]chromene-2,8-dione using L-proline as a novel and efficient catalyst

We report the high yield synthesis of novel 9-benzoyl-4-methylpyrano[2,3-f]chromene-2,8-dione derivatives obtained by the reaction of 8-formyl-7-hydroxy-4-methylcoumarin with various active methylene compounds. A mechanism of the tandem Knoevenagel condensation and cyclisation reaction is proposed. Structures of all compounds were elucidated on the basis of 1H and 13C NMR, and mass spectrometry, and elemental analysis.

Two novel aggregation-induced emission active coumarin-based Schiff bases and their applications in cell imaging

Two new coumarin-based Schiff bases, 8,8′-((1E,1′E)-hydrazine- 1,2-diylidenebis(methanylylidene))bis(7-hydroxy-4-methyl-2H-chromen-2-one), (CHC), and 7-hydroxy-8-((E)-((E)-((2-hydroxynaphthalen-1-yl)methylene)hydrazono) methyl)-4-methyl-2H-chromen-2-one, (CHN), with excited-state intramolecular proton-transfer (ESIPT) properties, were synthesized and characterized. Both of the compounds displayed aggregation-induced emission (AIE) characteristics, of which CHC nanoparticles emitted a reddish orange fluorescence, while the CHN nanoparticles exhibited a saffron yellow fluorescence. The appearance of emission peaks in the long wave regions with large Stokes-shifts demonstrated the occurrence of the ESIPT process. Observations of the nanoparticles' morphologies were undertaken through a transmission electron microscope (TEM) method. Furthermore, due to the good biocompatibilities, high stabilities and the large Stokes-shifts, the two compounds were ideal candidates for cell staining. This journal is the Partner Organisations 2014.

An enolato-bridged dinuclear Cu(ii) complex with a coumarin-assisted precursor: A spectral, magnetic and biological study

A new, phenoxo-bridged CuII dinuclear complex Cu2[(L)2(DMF)2] (1) has been obtained by employing the coumarin-assisted tridentate precursor, H2L, [benzoic acid(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl

Novel coumarin isoxazoline derivatives: Synthesis and study of antibacterial activities

A highly efficient and mild protocol for the syntheses of ethyl-3-[7-benzyloxy-4-methyl-2-oxo-2H-8-chromenyl]-5-aryl-4,5-dihydro-4-isoxazole carboxylates and ethyl-3-[7-benzyloxy-3-chloro-4-methyl-2-oxo-2H-8-chromenyl]-5-aryl-4,5-dihydro-4-isoxazole carboxylates in good yields via [3 + 2] cycloaddition of in situ–generated nitrile oxides from 7-benzyloxy-4-methyl-coumarin hydroxymoylchlorides and 7-benzyloxy-3-chloro-4-methyl-coumarin hydroxymoylchlorides respectively with ethyl-3-aryl prop-2-enoate has been developed. The new compounds are screened for antibacterial activity.

A novel coumarin-derived dithioacetal chemosensor for trace detection of Hg2+ in real water samples

A novel coumarin-derived dithioacetal chemosensor, 8-(1,3-dithian-2-yl)-7-hydroxy-4-methylcoumarin (LS), has been designed and synthesized. The sensor LS showed highly selective fluorescent sensing for Hg2+ with a low detection limit of 0.81 nM in the pH range from 6.15 to 9.96 in ethanol/water (1:1, v/v) solution. The sensing mechanism of LS toward Hg2+ was proposed and verified by 1H nuclear magnetic resonance spectroscopy studies. Under an ultraviolet lamp, the fluorescence color changes could be easily detected by the naked eye. In addition, the sensor LS has been applied in the trace detection of Hg2+ in real water samples.

A new unsymmetrical azine derivative based on coumarin group as dual-modal sensor for CN? and fluorescent “OFF–ON” for Zn2?+

A simple chemosensor YS based on coumarin group was designed and synthesized. Its structure was determined by single crystal X–ray diffraction analysis. In the presence of cyanide the sensor showed an immediate visible change in color from colorless to pale yellow by naked–eyes and produced a strong blue fluorescence rapidly in DMSO/H2O (3:7, v/v). The detection limit on fluorescence response of the sensor to CN? is down to 1.69?×?10??7?M. In addition YS could show fluorescence turn–on response rapidly for Zn2?+ over other metals ions such as Fe3?+, Hg2?+, Ag+, Ca2?+, Cu2?+, Co2?+, Ni2?+, Cd2?+, Pb2?+, Cr3?+ and Mg2?+ in aqueous solutions. Notably, this sensor served as a molecular switch, which was controlled by Zn2?+ and EDTA cyclically. Test strips based on YS were fabricated, which could act as a convenient and efficient CN? and Zn2?+ test kit. This chemosensor could achieve the detection of two ions, which need not depend on two different sensors.