67268-43-3Relevant articles and documents
An umbelliferone-derivated fluorescent sensor for selective detection of palladium(II)from palladium(0)in living cells
Zhang, Xu-Ping,Yuan, Qing,Qi, Ya-Lin,Zheng, Da-Jun,Liu, Qi-Xing,Wang, Bao-Zhong,Yang, Yu-Shun,Zhu, Hai-Liang
, (2019)
Palladium (Pd)has drawn worldwide attentions because its connections to industry, chemistry, biological material and public health. Quantitative and selective detection tools for Pd and its ion forms are in urgent necessity. Here an umbelliferone derivative Umb-Pd2 was provided as a small, steady, safe and selective sensor for detecting Pd(II). It indicated advantages including sensitive (LOD 1.1 nM), wide pH tolerance (5.0–10.0), applicable linear range (0–1.8 equivalent)and low toxicity. The most attractive point was its explicit selectivity towards Pd(II)from Pd(0)in both independent and coexistence systems. This distinguishing ability was further utilized in imaging in living cells, raising this work as a rare and important example among all the published papers on palladium sensing. Thus, Umb-Pd2 supplied a potential approach for further improvement and applications in both daily chemistry and public health.
Fluorescent probe 7-(prop-2-yn-1-yloxy)-2H-chromen-2-one: Experimental and DFT based approach to photophysical properties
Yadav, Neesha,Singh, Shailja,Mangawa, Shrawan Kumar,Dixit, Sandeep K.,Gupta, Ujval,Khajuria, Yugal,Awasthi, Satish Kumar
, p. 311 - 317 (2015)
Abstract Compound 7-(prop-2-yn-1-yloxy)-2H-chromen-2-one was synthesized by Pechmann condensation reaction and characterized by various spectroscopic techniques. The structure of title compound was confirmed by single crystal X-ray diffraction. The compound crystallized in the orthorhombic system with P 21 21 21 space group and the corresponding lattice parameters were found to be a = 4.0138 (11) ?, α = 90°; b = 23.536 (6) ?, β = 90°; c = 10.93 (2) ?, γ = 90°. The crystal packing of molecule showed that intermolecular hydrogen bonds C3-H3?O3 [D = 3.53 ?, C-13-H13?O2 [D = 3.67 a and intermolecular short interaction between C1-H1?C1-H1 [2.68 ? forms a dimeric unit which finally stabilizes the crystal packing in three dimensional network in the molecule. Absorption and emission spectra shows that compound is fluorescent with good Stoke shift values ranging between 57 and 62 nm. Thermal analysis further supports by TGA, DTA. The photophysical results show that the compound exhibits change in fluorescence quantum yield with change in solvent polarity. The structural parameters and the vibrational wave numbers obtained from the optimized geometry of the compound from DFT-B3LYP calculations employing 6-311G (d,p) basis set are in good agreement with the experimental data. UV-Vis spectrum calculated by employing time dependent density functional theory (TD-DFT) is also in very good agreement with the experiment for all solvents.
Expanding the Versatility of Dipicolinate-Based Luminescent Lanthanide Complexes: A Fast Method for Antenna Testing
Andres, Julien,Borbas, K. Eszter
, p. 8174 - 8176 (2015)
A dipicolinate (dpa)-based platform for the rapid testing of potential lanthanide-sensitizing antennae was developed; 4-methyl-7-O-alkylcoumarin-appended dpa could sensitize four lanthanides. The platform could be used to estimate the photophysical proper
Synthesis of energy transfer cassettes via click and Suzuki-Miyaura cross coupling reactions
Goel, Richa,Luxami, Vijay,Paul, Kamaldeep
, p. 37664 - 37671 (2016)
Novel cassettes capable of energy transfer involving simple synthetic methods viz., copper catalyzed azide-alkyne cycloaddition (click reaction) at the C-8 position and palladium catalyzed Suzuki-Miyaura cross coupling at the C-6 position have been represented. The resulting imidazo[1,2-a]pyrazine-triazole bridged coumarin cassettes are capable of energy transfer from a donor core to an acceptor moiety.
Synthesis of Tyrosol 1,2,3-Triazole Derivatives and Their Phytotoxic Activity against Euphorbia heterophylla
Franco, Cristiane Aparecida,da Silva, Toshik Iarley,Dias, Marlon Gomes,Ferreira, Bruno Wesley,de Sousa, Bianca Lana,Bousada, Guilherme Mateus,Barreto, Robert Weingart,Vaz, Boniek Gontijo,Lima, Gesiane da Silva,dos Santos, Marcelo Henrique,Grossi, José Ant?nio Saraiva,Vieira Varej?o, Eduardo Vinícius
, p. 2806 - 2816 (2022/03/16)
The synthesis and phytotoxic activity of a series of tyrosol 1,2,3-triazole derivatives are reported herein. Target compounds were synthesized through the copper(I)-catalyzed azide-alkyne cycloaddition reaction (CuAAC), known as click reaction, and these were tested for phytotoxic activity on leaves of wild poinsettia (Euphorbia heterophylla), fleabane (Conyza sumatrensis), and tropical spiderwort (Commelina benghalensis). These are three highly noxious agricultural weeds that challenge available weed control methods, including the use of chemical herbicides. Twenty-five compounds were synthesized and tested. None of the compounds showed phytotoxic activity against C. benghalensis and C. sumatrensis, but almost all of them produced yellowing, bleaching, and necrosis on leaves of E. heterophylla. Two of the tyrosol 1,2,3-triazole derivatives produced more extensive lesions than those produced by the commercial herbicide diquat, used as a positive control (p ≤ 0.05). When applied on leaves of E. heterophylla, these compounds interfered with the stomatal conductance, net photosynthesis, internal carbon concentration, transpiration rate, water-use efficiency, and chlorophyll A and B contents. The interference of such compounds on such photosynthesis-related variables indicates that tyrosol 1,2,3-triazole derivatives may be capable of lowering the competitiveness of E. heterophylla and acting as additional tools for managing this competitive weed in agricultural lands.
Inhibition of acetylcholinesterase by coumarin-linked amino acids synthetized via triazole associated with molecule partition coefficient
De Sousa, Bianca L.,Leite, Jo?o P.V.,Mendes, Tiago A.O.,Varej?o, Eduardo V.V.,Chaves, Anna C.S.,da Silva, Júnio G.,Agrizzi, Ana P.,Ferreira, Priscila G.,Pilau, Eduardo J.,Silva, Evandro,dos Santos, Marcelo H.
, p. 652 - 664 (2021/02/16)
A previous study for the identification of acetylcholinesterase (AChE) inhibitors demonstrated that the hybrid between tyrosol, the 1,2,3-triazole nucleus, and the coumarin group, namely 7-({1-[2-(4-hydroxyphenyl)ethyl]-1H-1,2,3-triazol-4-yl}methoxy)-4-methyl-2H-chromen-2-one (10), has a high enzyme inhibitory activity. Here, we synthesized analogues of 10 via triazole with pharmacophoric groups represented by tyrosine, phenylalanine, tryptophan, and glycine in addition to evaluating the impact of coumarin-linked amino acids on AChE inhibition. We obtained eight triazoles, six of which are undescribed. In general, the presence of carboxylic acid decreased the inhibitory activity, while aromatic amino acids increased enzymatic inhibition compared to glycine. The derivative containing tyrosine, structurally most similar to 10, presented the lowest inhibition percentage, indicating that phenolic hydroxyl is not the preponderant factor for inhibition. Molecular docking was not enough to explain in vitro experiments. On the other hand, MlogP (logP calculated by the Moriguchi method) was related positively to enzymatic inhibition. To increase the hydrophobicity of the molecules, we tested the esterified triazole derivatives comparatively with the enzyme. The compound ethyl 2-(4-(((4-methyl-2-oxo-2H-chromen-7-yl)oxy)methyl)- 1H-1,2,3-triazol-1-yl)acetate (6) presented an increment of inhibitory activity of 46.97 ± 1.75% at 100 μmol L-1. We also associated the best activity with the lowest van der Waals volume and molar mass values.
Comprehensive Investigation of the Photophysical Properties of Alkynylcoumarin Gold(I) Complexes
Aullón, Gabriel,Cunha, Carla,Lima, Jo?o Carlos,Pinto, Andrea,Rodríguez, Laura,Seixas De Melo, J. Sérgio
, p. 11751 - 11760 (2021/11/13)
Six gold(I) complexes (R3P-Au-Coum) containing three different alkynylcoumarin chromophores (Coum) with different electron-donating and electron-withdrawing characteristics and two different water-soluble phosphanes (PR3= PTA (a) and DAPTA (b)) have been synthesized (1ab, unsubstituted coumarin; 2a b , 4-methyl substituted coumarin; 3a b , 3-chloro and 4-methyl substituted coumarin). A comprehensive study of the photophysical properties of the R3P-Au-Coum, together with their propynyloxycoumarin precursors 1 - 3 , was performed in solution at room and low temperatures. Spectral and photophysical characteristics of the R3P-Au-Coum essentially depend on the electronic characteristics of the propynyloxycoumarin ligand. The presence of the Au(I) atom was found to be responsible for an increase of the intersystem crossing, with triplet state quantum yield values, ?T, ranging from ～0.05 to 0.35 and high coumarin phosphorescence quantum yield values for derivatives 1 and 2 ; fluorescence dominates the deactivation in derivatives 3 . Efficient singlet oxygen photosensitization was observed for the new compounds 3a b . From TDDFT calculations, the relevant HOMO and LUMO of the compounds, i.e., those involved in the transitions, are dominated by the frontier orbitals associated with the coumarin core. The Au(I)-phosphane structure introduces a new transition assigned to an intraligand transition involving the phosphane ligand, and π(C≡C) system, to theporbitals of phosphorus and gold atoms.
