13373-28-9

Usage

InChI:InChI=1/C12H9NO6/c1-2-18-11(14)9-6-7-5-8(13(16)17)3-4-10(7)19-12(9)15/h3-6H,2H2,1H3

Upstream product

• 64-17-5 ethanol 
• 10242-15-6 6-nitro-2-oxo-2H-chromen-3-carboxylic acid 
• 1846-76-0 ethyl coumarin-3-carboxylate 
• 97-51-8 5-Nitrosalicylaldehyde 
• 105-56-6 ethyl 2-cyanoacetate 
• 107-91-5 cyanoacetic acid amide 
• 39224-61-8 2-hydroxy-5-nitrobenzyl alcohol 
• 3702-98-5 ethyl 4,4,4-trichloroacetoacetate 
• 2033-24-1 cycl-isopropylidene malonate 
• 16634-91-6 2-methyl-5-nitro-benzaldehyde 
• 105-53-3 diethyl malonate 
• 161956-34-9 ethyl 4-(2,2-diamino-1-ethoxycarbonylethenyl)-6-nitro-2-oxochroman-3-carboxylate 

Downstream Products

• 91587-88-1 5-amino-2-carboxylic acid coumarin 
• 324066-77-5 6-nitro-2-oxo-N-o-tolyl-2H-chromene-3-carboxamide 
• 302815-22-1 N-(2-methoxyphenyl)-6-nitro-2-oxo-2H-chromene-3-carboxamide 
• 301818-29-1 6-nitro-2-oxo-N-m-tolyl-2H-chromene-3-carboxamide 
• 317327-45-0 6-nitro-2-oxo-N-(3-(trifluoromethyl)phenyl)-2H-chromene-3-carboxamide 
• 1614257-64-5 S-4-bromophenyl 6-nitro-2-oxo-2H-chromene-3-carbothioate 

Relevant academic research and scientific papers

Ultrasensitive and selective fluorescent sensor for cysteine and application to drug analysis and bioimaging

A fluorescent sensor based on coumarin-maleimide conjugate was developed for efficient discrimination of Cys from Hcy and GSH in both organic and aqueous solution. Addition of Cys to the non-fluorescent sensor solution in DMF induced bright blue fluorescence and enhanced the fluorescence intensity by 320-fold while other amino acids and biothiols (Gly, Hcy, GSH, Glu, Val, Tyr, Arg, Trp, Lys, His, Leu, Phe, Asp and Met) did not bring about remarked change. The sensor responds to Cys extremely rapidly. If Cys was added to the sensor solution, the fluorescence intensity increased by 170-fold immediately and attained the maximum value in 5 min. A linear relationship was observed between Cys concentration within 2–20 μM and the fluorescence intensity of the sensor solution. The detection limit of the sensor toward Cys is as low as 4.7 nM. The sensor is also effective for specific detection of Cys in aqueous (DMF/H2O = 9:1, v/v) solution. Practical application of the sensor to drug analysis and bioimaging of living Hela cells has been verified. Possible sensing mechanism of the sensor toward Cys has been proposed.

A green method for the synthesis of 3-substituted coumarins catalyzed by L-lysine in water via knoevenagel condensation

L-lysine was applied to the synthesis of 3-substituted coumarins through the condensation of various salicylaldehyde with reactive methylene compounds in water. In this work, waste minimization, catalyst recovery, simple operation and easier product work-up were achieved.

Synthesis and spectral study of novel benzopyrone and quinolinone derivatives

A series of novel benzopyrones and quinolinone derivatives were prepared using the readily obtainable 6-nitrobenzo- 2-pyron-3-carboxylate through the reaction with nitrogen nucleophilic reagents such as cyclohexyl amine, p-aminoacetophenone, diamines, hydrazine hydrate, thiosemicarbazide, anthranilic acid and carbon nucleophile as malononitrile. The IR, 1H NMR and mass spectra of the new synthesised compounds were discussed. Website

Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors

Abstract Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study.

Effect of conformational flexibility on photophysics of bis-coumarins

The fluorescence intensity of bis-coumarins linked via CONH and COO functionalities are shown to exhibit a strong dependance on solvent polarity. The presence of the intramolecular hydrogen bond between the CO oxygen atom of coumarin and amide-NH moieties reduces the number of thermodynamically populated conformations in both ground and electronically excited states and an anti-arrangement of coumarin units is favored. Additionally, the rigidity of the linker raises the barrier to the conical intersection with the ground state, and in non-polar solvents strong fluorescence is observed. Although changing the CONH linking position from 3-7′ to 3-6′, does not remarkably affect the photophysics, replacement with a flexible ester linker allows the molecule a greater degree of conformational freedom due to the absence of the intramolecular hydrogen bonding interaction. The photophysical effect of this is the appearance of two fluorescence bands, the relative intensity and spectral positions of which are sensitive to the environment. Theoretical explorations of the excited-state potential energy surfaces performed with the aid of the ADC(2) ab initio electronic structure theory method revealed an exceptional wealth of concomitant photophysical processes. In particular, two channels for radiationless deactivation of the excited state were found; the first is related to the inter-ring twist of the coumarin units, and the second is associated with the excited-state intramolecular proton-transfer (ESIPT) from the CONH linker to the coumarin core.

One-pot preparation of coumarins by Knoevenagel condensation in solvent-free condition under microwave irradiation

3-Substituted coumarins were prepared by the Knoevenagel reaction of 2-hydroxybenzaldehyde derivatives and 2-hydroxy-1-naphthaldehyde in the presence of ammonium aceteate on basic alumina or silica gel under microwave irradiation. High yields, low reaction times, being environmentally friendly, elimination of organic base and solvent are advantages of this method.

Supramolecular synthesis of coumarin derivatives catalyzed by a coordination-assembled cage in aqueous solution

A self-assembled Pd4L2 cage is employed as a water-soluble molecular flask for the synthesis of functionalized coumarins from a series of salicylaldehyde derivatives and cyanoacetates/malononitrile. The catalytic reaction features mild aqueous conditions and broad substrate scope. Crystal structures of the host-guest complexes for two substrates and one analogous intermediate have been obtained, shedding light on the supramolecular reaction mechanism. Michaelis-Menten kinetic studies were performed in one typical case, revealing that the rate of product formation has been enhanced by over 23-fold in contrast to the background reaction without cage. Moreover, the same reaction catalyzed by a smaller Pd6L4 cage gives a mixture of products and much lower yields, suggesting that fine-tuning on the size and symmetry of the cages’ cavity is crucial for their applications in supramolecular catalysis.

Novel coumarin-based fluorescent probe for selective detection of Cu(II)

Abstract We report an efficient and convenient method for preparing nitro-3-carboxamide coumarin derivatives, proposed as novel fluorescent chemosensor, through microwave irradiation. This compound can be used as fluorescent probe for Cu2+ with selectivity over other metal ions in aqueous solution. The fluorescence of 6-nitro-N-[2-(dimethylamino)ethyl]-2-oxo-2H-chromene-3-carboxamide(3) is the highest in the presence of Cu2+, with stronger excitation at λ = 320 nm than for the other cations tested. copy; 2015 Elsevier B.V.

Preparative-scale synthesis of amino coumarins through new sequential nitration and reduction protocol

In contrast to the conventional deleterious approach for nitration (for example HNO3/H2SO4) and for reduction (for example Zn/HCl), we hypothesized that sensitive heterocycles such as coumarins could not withstand with those hard conditions. Hence, while studying this reaction sequence to prepare amino coumarins (which is our ongoing project to synthesize antitubercular coumarin agents), we came across mild and greener reagent for nitration using calcium nitrate (Ca(NO3)2·4H2O; lime nitrate), and reduction using D-glucose. These two mild, chemoselective, high yielding methods are discussed herein.

Michael adducts from 6-nitrocoumarins and enaminoesters

Addition of the enaminoesters 2a-d to the 6-nitrocoumarins 1a-d gave 3 or 5. The aminocrotonic esters 2a,b underwent competitive addition of their C-4-methyl groups to yield 6a,b as by-products. Benzopyrano[3,4-c]pyridine derivatives 4b and 7-9 have been obtained from the adducts under various conditions. Some of the adducts have been converted by acidic hydrolysis into the amides 10 which have also been prepared directly by addition of ethylmalonamate to 1b-d.