54711-39-6Relevant articles and documents
Design and synthesis of 7-diethylaminocoumarin-based 1,3,4-oxadiazole derivatives with anti-acetylcholinesterase activities
Yu, Xiang,Zhao, You-Fang,Huang, Guo-Juan,Chen, Ya-Fang
, p. 866 - 876 (2021)
Twelve novel 7-diethylaminocoumarin-based 1,3,4-oxadiazole derivatives were synthesized via iodine-mediated oxidative cyclisation and confirmed by 1H NMR, 13C NMR and HRMS. The result of these derivatives' activities inhibiting acetylcholinesterase in?vitro showed that 4 g and 4i had moderate inhibitory activities with 69.19% and 65.06%, respectively. The preliminary structure-activity relationships revealed that introduction of halogen atom on the para-position of phenyl of 7-diethylaminocoumarin-based 1,3,4-oxadiazole derivatives could enhance their activities. Molecular docking study suggested that 4 g possessed an optimal docking pose with interactions inside AChE.
Photo-controlled release of fipronil from a coumarin triggered precursor
Gao, Zhenhong,Yuan, Pengtao,Wang, Donghui,Xu, Zhiping,Li, Zhong,Shao, Xusheng
, p. 2528 - 2535 (2017)
Developing efficient controlled release system of insecticide can facilitate the better use of insecticide. We described here a first example of photo-controlled release of an insecticide by linking fipronil with photoresponsive coumarin covalently. The generated coumarin-fipronil (CF) precursor could undergo cleavage to release free fipronil in the presence of blue light (420?nm) or sunlight. Photophysical studies of CF showed that it exhibited strong fluorescence properties. The CF had no obvious activity against mosquito larvae under dark, but it can be activated by light inside the mosquito larvae. The released Fip from CF by blue light irradiation in vitro retained its activity to armyworm (Mythimna separate) with LC50 value of 24.64?μmol?L?1. This photocaged molecule provided an alternative delivery method for fipronil.
Light-induced antibiotic release from a coumarin-caged compound on the ultrafast timescale
Herzig,Elamri,Schwalbe,Wachtveitl
, p. 14835 - 14844 (2017)
A synthesis route for puromycin caged with the photo-responsive 7-diethylaminocoumarinyl protecting group carbamate was developed. The inactivation and recovery of the cytotoxic effect of puromycin was tested with a XTT cell viability assay. The uncaging mechanism was studied by ultrafast transient absorption spectroscopy and by time-correlated single photon counting. The combination of these results with quantum-chemical calculations provided detailed insights in dynamics upon excitation. Interestingly, a change of the dipole moment due to structural rearrangements of the amino moiety led to an intermolecular charge transfer on the picosecond time-scale. IR measurements marked the successful uncaging via the release of CO2, resulting from the carbamate linker. This decarboxylation constituted the rate-limiting step of the uncaging reaction and occurred on the subsecond timescale. DEACM-puromycin, thus, represents an efficient photo-activatable antibiotic for in-cell applications.
Green-Light Activatable, Water-Soluble Red-Shifted Coumarin Photocages
Bojtár, Márton,Kormos, Attila,Kis-Petik, Katalin,Kellermayer, Miklós,Kele, Péter
, p. 9410 - 9414 (2019)
Easily accessible green-light activatable (>500 nm) photocages based on red-shifted, π-extended coumarin scaffolds are developed with uncaging efficiencies similar to those of recently introduced BODIPY derivatives. The photocages possess increased aqueous solubility, high absorption coefficients within the 450-600 nm range, and exceptionally high two-photon cross sections.
Synthesis, photophysical, photochemical, and computational studies of coumarin-labeled nicotinamide derivatives
Bourbon, Pauline,Peng, Qian,Ferraudi, Guillermo,Stauffacher, Cynthia,Wiest, Olaf,Helquist, Paul
, p. 2756 - 2762 (2012)
The syntheses and photophysical/photochemical properties of two amide-tethered coumarin-labeled nicotinamides are described. Photochemical studies of 6-bromo-7-hydroxycoumarin-4-ylmethylnicotinamide (BHC-nicotinamide) revealed an unexpected solvent effect. This result is rationalized by computational studies of the different protonation states using TD-DFT with the M06L/6-311+G** method with implicit and explicit solvation models. Molecular orbital energies responsible for the λmax excitation show that the functionalization of the coumarin ring results in a strong red-shift from 330 to 370 nm when the pH of solution is increased from 3.06 to 8.07. From this MO analysis, a model for solvent interactions has been proposed. The BHC-nicotinamide proved to be photochemically stable, which is also interpreted in terms of NBO calculations. The results provide a set of principles for the rational design of either photostable labeling reagents or photolabile cage compounds.
Synthesis of Fluorescent Amino Acids via Palladium-Catalyzed Allylic Alkylations
Schmidt, Lisa,Doroshenko, Tamara,Barbie, Philipp,Grüter, Andreas,Jung, Gregor,Kazmaier, Uli
, p. 3077 - 3086 (2016)
Coumarin-derived allylic carbonates are found to be suitable electrophiles for the synthesis of fluorescent amino acids via palladium-catalyzed allylic alkylation of chelated glycine enolates. The formation of regioisomers can be suppressed by proper choice of the allyl carbonate.
Sequential Uncaging with Green Light can be Achieved by Fine-Tuning the Structure of a Dicyanocoumarin Chromophore
Gandioso, Albert,Palau, Marta,Nin-Hill, Alba,Melnyk, Ivanna,Rovira, Carme,Nonell, Santi,Velasco, Dolores,García-Amorós, Jaume,Marchán, Vicente
, p. 375 - 384 (2017)
We report the synthesis and photochemical properties of a series of dicyanocoumarinylmethyl (DEAdcCM)- and dicyanocoumarinylethyl (DEAdcCE)-based photocages of carboxylic acids and amines with absorption maximum around 500 nm. Photolysis studies with green light have demonstrated that the structure of the coumarin chromophore as well as the nature of the leaving group and the type of bond to be photocleaved (ester or carbamate) have a strong influence on the rate and efficiency of the uncaging process. These experimental observations were also supported by DFT calculations. Such differences in deprotection kinetics have been exploited to sequentially photolyze two dicyanocoumarin-caged model compounds (e.g., benzoic acid and ethylamine), and open the way to increasing the number of functional levels that can be addressed with light in a single system, particularly when combining dicyanocoumarin caging groups with other photocleavable protecting groups, which remain intact under green light irradiation.
Four levels of wavelength-selective uncaging for oligonucleotides
Rodrigues-Correia, Alexandre,Weyel, Xenia M. M.,Heckel, Alexander
, p. 5500 - 5503 (2013)
In this study the new nucleobase-caged nucleotides dTNpHP and dTDEACM are introduced. Together with two other caging groups (NDBF and NPP) this results in four layers of wavelength-selective uncaging for oligonucleotides, sequentially going from 505 to 440 nm, 365 nm, and finally to 313 nm for the photolysis reaction.
Light-triggered release of insecticidally active spirotetramat-enol
Xu, Zhiping,Gao, Zhenhong,Shao, Xusheng
, p. 1648 - 1650 (2018)
Spirotetramat metabolizes to its active enol form in the plant. We described here a photocaged pesticide delivery system that can release insecticidal spirotetramat enol form upon light irradiation. Covalently linking spirotetramat-enol with photoresponsive coumarin generated the caged insecticide. The photophysical and photochemical properties, deprotection photolysis and insecticidal activities of the caged spirotetramat enol were studied. This light-triggered system can undergo cleavage to release free spirotetramat enol form at the presence of blue light (420 nm) or sunlight. Bioassays indicated that the triggered molecule has no obvious insecticidal activity against Aphis craccivora Koch at dark and could be activated by light to release the insecticidal ingredients, which provides precise control over insecticide delivery.
Melding Caged Compounds with Supramolecular Containers: Photogeneration and Miscreant Behavior of the Coumarylmethyl Carbocation
Kamatham, Nareshbabu,Da Silva, José P.,Givens, Richard S.,Ramamurthy
, p. 3588 - 3591 (2017)
By merging well-established concepts of supramolecular chemistry, protecting group strategy, and photochemistry, we have solubilized in water hydrophobic organic molecules consisting of a photoactive protecting group and masked carboxylic acids, released the desired acid, and confined a reactive carbocation intermediate within a capsule. Confinement of the photogenerated carbocation brought out the latent radical-like behavior. This observation is consistent with the recent theoretical prediction of the 7-(diethylamino)coumarinyl-4-methyl carbocation having a triplet diradical ground-state electronic contribution.
