142730-52-7

Usage

Uses

Used in Organic Chemistry Research:
10-OXO-2,3,5,6-TETRAHYDRO-1H,4H,10H-11-OXA-3A-AZA-BENZO[DE]ANTHRACENE-9-CARBALDEHYDE is used as a research compound for studying its chemical properties and potential reactions with other molecules. Its unique structure and aldehyde functional group make it a valuable subject for exploring new organic synthesis pathways and mechanisms.
Used in Material Science:
In the field of material science, 10-OXO-2,3,5,6-TETRAHYDRO-1H,4H,10H-11-OXA-3A-AZA-BENZO[DE]ANTHRACENE-9-CARBALDEHYDE is utilized as a precursor or building block for the development of new materials with specific properties. Its aromatic nature and complex structure may contribute to the creation of novel materials with applications in various industries, such as pharmaceuticals, electronics, or advanced materials.
Used in Pharmaceutical Development:
10-OXO-2,3,5,6-TETRAHYDRO-1H,4H,10H-11-OXA-3A-AZA-BENZO[DE]ANTHRACENE-9-CARBALDEHYDE is employed as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its unique structure may offer new opportunities for the development of drugs with novel mechanisms of action or improved therapeutic properties.
Used in Chemical Synthesis:
As an aldehyde, 10-OXO-2,3,5,6-TETRAHYDRO-1H,4H,10H-11-OXA-3A-AZA-BENZO[DE]ANTHRACENE-9-CARBALDEHYDE can be used in various chemical synthesis processes, such as the formation of imines, hydrazones, or oximes. Its reactivity and functional groups make it a versatile compound for creating new chemical entities with potential applications in various fields.
Used in Analytical Chemistry:
10-OXO-2,3,5,6-TETRAHYDRO-1H,4H,10H-11-OXA-3A-AZA-BENZO[DE]ANTHRACENE-9-CARBALDEHYDE can be utilized as a reference compound or standard in analytical chemistry for the development and validation of analytical methods. Its unique structure and properties may be useful for testing the performance of chromatographic, spectroscopic, or other analytical techniques.
Used in Environmental Applications:
The complex structure of 10-OXO-2,3,5,6-TETRAHYDRO-1H,4H,10H-11-OXA-3A-AZA-BENZO[DE]ANTHRACENE-9-CARBALDEHYDE may have potential applications in environmental chemistry, such as the development of new methods for the detection or remediation of pollutants. Its chemical properties could be harnessed to create novel sensors or adsorbents for environmental monitoring and protection.
Used in Nanotechnology:
10-OXO-2,3,5,6-TETRAHYDRO-1H,4H,10H-11-OXA-3A-AZA-BENZO[DE]ANTHRACENE-9-CARBALDEHYDE may be employed in the field of nanotechnology as a component of nanomaterials or as a template for the synthesis of nanostructures. Its complex molecular architecture could contribute to the development of new materials with unique electronic, optical, or mechanical properties.
Used in Dye and Pigment Industry:
The aromatic properties of 10-OXO-2,3,5,6-TETRAHYDRO-1H,4H,10H-11-OXA-3A-AZA-BENZ

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Relevant academic research and scientific papers

A highly selective water-soluble optical probe for endogenous peroxynitrite

A colorimetric and fluorescent probe C-Py-1 for ONOO- was prepared and it could exhibit high sensitivity and excellent selectivity toward ONOO- among reactive oxygen species (ROS) and reactive nitrogen species (RNS) with a rapid response time in 100% water solution. Meanwhile, C-Py-1 was successfully applied in the imaging of endogenous ONOO- in RAW264.7 cells.

Tyrosine specific sequential labeling of proteins

We report (a) on the synthesis of a long-wavelength fluorescent coumarin containing an allyloxy acetate moiety, (b) the synthesis of two linkers containing an allyloxy acetate and an alkyne or azide function, respectively, and (c) the selective modification human serum albumin by a sequential method involving Pd(II) catalyzed modification of the phenolic side chain of tyrosine residues with an alkyne bearing linker and a subsequent azide-alkyne click reaction with an azide functionalized long-wavelength emitting coumarin dye. The method is likely to be applicable to various kinds of azido-modified fluorophores, and the Pd(II)-catalyzed modification of the tyrosines may also be used to introduce other kinds of tags. With these reagents, tyrosine specific modulation of proteins and peptides becomes possible either directly or in a sequential manner.

Rationally designed fluorescence turn-on sensors: A new design strategy based on orbital control

Herein, we explore a new strategy in the chemo-sensor field for fluorescence amplification upon binding with metal ions based on controlled participation of the nitrogen lone pair orbital. The basic architecture of the sensor entails a fluorophore, the sp2 hybridized nitrogen lone pair (-C=N-), and a chelator site referred to as the control part. Though nonplanar and nonfluorescent, compound IC1 achieved pseudo planarity from binding with Zn2+ as indicated by the increased fluorescence signal. Its other analogue (IC2) is also planar, and unlike IC1-Zn2+ was fluorescent with a lack of binding affinity to metal ions. The time-dependent density functional theory (TDDFT) calculations revealed that the fluorescence amplification was due to the blocking of the nitrogen lone pair orbital; unlikely geometrical rearrangements were insignificant. This could indicate a breakthrough concept in the future design of fluorescent turn-on sensors.

A highly sensitive fluorescent probe for the detection of bisulfite ion and its application in living cells

A novel direct visualisation, fluorescent probe derived from coumarin for bisulfate ion detection has been designed and synthesized. This probe shows a rapid, high selectivity, and sensitivity in the detection of bisulfate ion. In a solution of DMSO:HEPES (1:9, v:v, 10 mM, pH 7.4) buffer containing the probe, the presence of HSO3? made the UV–vis absorption of the probe blue-shift from pink to yellow, and the fluorescence of the probe also changed from red to green. Other investigated analytes and ions did not disturb the determination of HSO3?. The reaction mechanism of the determination was proposed based on the nucleophilic attack toward electron-poor C[dbnd]C bond of the probe. This probe has been successfully applied for determination of HSO3? in living cells.

Live-cell imaging of lipid droplets using solvatochromic coumarin derivatives

Lipid droplets (LDs), the lipid-rich intracellular organelles, serve to regulate many physiological processes and therefore attention has been attracted towards their selective detection. We report positively solvatochromic lipophilic dyes, based on the push-pull framework containing coumarin-pyridine heterocycles for selective live-cell imaging of lipid droplets (LDs) in Cos-7 and McA-RH7777 cells at ultralow concentrations (200 nM). The fluorescent probes show a remarkable increase in fluorescence intensity with time with the hydrophobic core of the lipid droplets contributing to the observed intensity enhancement. The simple structural framework, red emission, strong Stokes shift (>80 nm), and excellent biocompatibility highlight their significance as a versatile imaging tool for studying lipid droplets (LDs).

Development of a coumarin-based fluorescent probe for hydrogen peroxide based on the Payne/Dakin tandem reaction

Hydrogen peroxide (H2O2) is associated with many physiological and pathological processes in biological systems. Here, we report 7-diethylamino-3-formyl-coumarin (Cou-CHO) as a turn-on fluorescent probe for H2O2. The proposed probe employs a tandem Payne/Dakin reaction to convert the electron-withdrawing aldehyde to the electron-donating hydroxyl group, thus hindering the formation of twisted intramolecular charge transfer (TICT) state of 7-diethylaminocoumarin, and thereby resulting in a fluorescence turn-on response. Cou-CHO features high specificity, excellent sensitivity and fast response toward H2O2. In particular, Cou-CHO enables the direct visualization of basal and endogenously produced H2O2 in living cells. The results demonstrate that the tandem Payne/Dakin reaction can provide a new choice to develop H2O2-selective probes.

KCN sensor: Unique chromogenic and 'turn-on' fluorescent chemodosimeter: Rapid response and high selectivity

An indole conjugated coumarin 1 for KCN chemodosimeter has been prepared and displayed considerable dual changes in both absorption (blue-shift) and emission (turn-on) bands exclusively for KCN. DFT/TDDFT calculations support that the fluorescence enhancement of 1-KCN is mainly due to blocking of the ICT process. The Royal Society of Chemistry.

Coumarin-based thiol chemosensor: Synthesis, turn-on mechanism, and its biological application

A new chemodosimetric probe (1) is reported that selectively detects thiols over other relevant biological species by the turning on of its fluorescence through a Michael type reaction. The fluorogenic process upon its reaction was revealed to be mediated by intramolecular charge transfer, as confirmed by time-dependent density functional theory calculations. The application of probe 1 to cells is also examined by confocal microscopy, and its cysteine preference was observed by an ex vivo LC-MS analysis of the cellular metabolite.

A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation

Triazolopyridines are an important kind of fused-ring compounds. A HOCl-promoted triazolopyridine formation strategy is reported here for the first time in which hypochlorous acid (HOCl) mildly and efficiently promotes the formation of 1,2,4-triazolo[4,3-a]pyridines NT1-NT6 from various 2-pyridylhydrazones N1-N6. N6, a rhodol-pyridylhydrazone hybrid, was developed into a fluorescent probe for the selective detection of HOCl, and successfully applied to probe endogenous HOCl in living cells and zebrafish in situ and in real time. The present intramolecular cyclization reaction is selective and atom-economical, thereby not only providing an important approach for the convenient synthesis of triazolopyridines, but also offering a general strategy for sensitive, selective and biocompatible detection of endogenous HOCl in complex biosystems.

Near-infrared fluorescent probe for simultaneously detecting DNA and RNA under double channels as well as preparation method and application of the near-infrared fluorescent probe

The invention discloses a fluorescent probe for simultaneously detecting DNA and RNA in cells under double channels as well as a preparation method and application of the fluorescent probe. The structure of the fluorescent probe is shown as a formula (I) or (II), wherein the Ar is an aromatic ring or an aromatic heterocyclic ring; the R1 and R2 are respectively and independently hydrogen, N-piperazine, N-methyl piperazine, -NH(CH2)nR3 and -NR3R4; the n is any integer from 1 to 5, and R3 and R4 are respectively and independently hydrogen, C1-C5 alkyl or C1-C5 haloalkyl; the A- is halide ions orp-toluenesulfonic acid ions. The fluorescent probe disclosed by the invention can be used for simultaneously detecting DNA and RNA in vitro and in cells under double channels; meanwhile, the fluorescent probe has the characteristics of rapid synthesis, near-infrared emission wavelength, good light stability, high detection sensitivity and the like, and is convenient to popularize and apply.