58336-35-9

Usage

Uses

Used in Pharmaceutical Industry:
2,3,5,6-1H,4H-TETRAHYDROQUINOLIZINO[9,9A,1-GH]COUMARIN is used as a lead compound for the development of new pharmaceutical agents due to its various biological and pharmacological activities, including anti-inflammatory, antitumor, and antimicrobial properties. Its unique structure and functional groups make it an interesting target for synthetic chemists and medicinal chemists.
Used in Biochemical Research:
In the field of biochemistry, 2,3,5,6-1H,4H-TETRAHYDROQUINOLIZINO[9,9A,1-GH]COUMARIN is used as a subject of study to understand its molecular conformation and interactions with biological targets. This research can provide insights into the compound's mechanism of action and potential applications in drug development.
Used in Pharmacology Research:
2,3,5,6-1H,4H-TETRAHYDROQUINOLIZINO[9,9A,1-GH]COUMARIN is utilized in pharmacological research to explore its potential as a therapeutic agent. Researchers investigate its pharmacological properties, such as its anti-inflammatory, antitumor, and antimicrobial activities, to determine its efficacy and safety for potential clinical use.

InChI:InChI=1/C15H15NO2/c17-13-6-5-11-9-10-3-1-7-16-8-2-4-12(14(10)16)15(11)18-13/h5-6,9H,1-4,7-8H2

Upstream product

• 63149-33-7 9-formyl-8-hydroxyjulolidine 
• 1779-58-4 (methyloxycarbonylmethyl)triphenylphosphonium bromide 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 105-53-3 diethyl malonate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 591-27-5 m-Hydroxyaniline 
• 536-90-3 m-Anisidine 
• 55804-66-5 ethyl 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f ]-pyrido[3,2,1-ij]quinoline-10-carboxylate 
• 213481-01-7 9-hydroxy-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one 
• 41175-50-2 8-hydroxyjulolidine 

Downstream Products

• 142730-52-7 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carbaldehyde 
• 521306-75-2 2-[(10-oxo-2,3,5,6-tetrahydro-1H,4H,10H-11-oxa-3a-aza-benzo[de]anthracen-9-yl)-phenyl-phosphanyl]-benzoic acid methyl ester 

Relevant academic research and scientific papers

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.

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.

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).

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.

Synthesis of 7-Azido-3-Formylcoumarin – A Key Precursor in Bioorthogonally Applicable Fluorogenic Dye Synthesis

Coumarins represent an important group of natural products and a common part of various drugs and fluorescent dyestuffs. Herein, we present the synthesis of a coumarin that can serve as a key starting material in the design and synthesis of bioorthogonally applicable fluorogenic dyes. The synthesis of 7-azido-3-formylcoumarin started from 7-diallylaminocoumarin. This allyl protected aminocoumarin is otherwise hard to obtain by conventional methods but was conveniently accessed in good yields by a sequential, Wittig-reaction–UV isomerization process. This sequential approach was studied in more details and applied for the synthesis of a series of substituted coumarins even in one-pot.

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.

A universal fluorogenic switch for Fe(II) ion based on N-oxide chemistry permits the visualization of intracellular redox equilibrium shift towards labile iron in hypoxic tumor cells

Iron (Fe) species play a number of biologically and pathologically important roles. In particular, iron is a key element in oxygen sensing in living tissue where its metabolism is intimately linked with oxygen metabolism. Regulation of redox balance of labile iron species to prevent the generation of iron-catalyzed reactive oxygen species (ROS) is critical to survival. However, studies on the redox homeostasis of iron species are challenging because of a lack of a redox-state-specific detection method for iron, in particular, labile Fe2+. In this study, a universal fluorogenic switching system is established, which is responsive to Fe2+ ion based on a unique N-oxide chemistry in which dialkylarylamine N-oxide is selectively deoxygenized by Fe2+ to generate various fluorescent probes of Fe2+-CoNox-1 (blue), FluNox-1 (green), and SiRhoNox-1 (red). All the probes exhibited fluorescence enhancement against Fe2+ with high selectivity both in cuvette and in living cells. Among the probes, SiRhoNox-1 showed an excellent fluorescence response with respect to both reaction rate and off/on signal contrast. Imaging studies were performed showing the intracellular redox equilibrium shift towards labile iron in response to reduced oxygen tension in living cells and 3D tumor spheroids using SiRhoNox-1, and it was found that the hypoxia induction of labile Fe2+ is independent of iron uptake, hypoxia-induced signaling, and hypoxia-activated enzymes. The present studies demonstrate the feasibility of developing sensitive and specific fluorescent probes for Fe2+ with refined photophysical characteristics that enable their broad application in the study of iron in various physiological and pathological conditions.

Preparation method of large emission wavelength fluorescent dye

The invention discloses a preparation method of a large emission wavelength fluorescent dye, comprising the following steps: first, modifying a naphthalimide by three-step reaction to obtain naphthalimide with activated methyl; second, carrying out four-step reaction to obtain aldehyde modified coumarin; third, reacting the naphthalimide with the activated methyl with the aldehyde modified coumarin to obtain a target product, the large emission wavelength fluorescent dye. Compared with the existing fluorescent dyes, the fluorescent dye synthesized in the invention has a near-infrared emission spectrum and Stokes shift up to 150 nm and is applicable to the fields such as laser, electroluminescence and fluorescent probes.

3-KETOCOUMARINES FOR LED PHOTOCURING

The present invention relates to 3-ketocoumarines which can be used as photoinitiators in LED photocuring and to a process for curing compositions comprising said 3-ketocoumarines.

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.