3949-36-8Relevant academic research and scientific papers
Two coumarin-based turn-on fluorescent probes based on for hypochlorous acid detection and imaging in living cells
Wang, Qingming,Jin, Lei,Wang, Wenling,Dai, Lihui,Tan, Xiaoxue,Zhao, Cong
, p. 239 - 245 (2019)
This work, two turn-on fluorescent probes (3-acetyl-2H-chromen-2-one (ACO) & (1E)-1-(1-(2-oxo-2H-chromen-3-yl)ethylidene)thiosemicarbazide (CETC)) based on coumarin have been designed and synthesized, which could selectively and sensitively recognize ClO? with fast response time. ACO & CETC were almost non fluorescent possibly due to both the lacton form of coumarin and unbridged C[dbnd]N bonds which can undergo a nonradiative decay process in the excited state. Upon the addition of ClO?, ACO & CETC were oxidized to ring - opened by cleavage the C–O and C[dbnd]N and the fluorescence intensity were increased considerably. Fluorescence titration experiments showed that the detection limit ACO & CETC is as low as 22 nm and 51 nm respectively. In particular, some relevant reactive species, including [rad]OH, 1O2, H2O2, KO2, some anions and cations cannot be interference with the test. In live cell experiments, ACO & CETC were successfully applied to image exogenous ClO? in HepG2 cells. Therefore, ACO & CETC not only could image ClO? in living cells but also proved that C–O and C[dbnd]N can be cleavage by ClO?.
Synthesis of some substituted pyrimidines derived from 3-acetyl coumarin
Al-Radha, Nabeel A.A.,Jaber, Qassim A.H.
, p. 3687 - 3691 (2015)
This study targets mainly the synthesis of a number of derivatives of coumarin containing ring pyrimidin-2-one substitutes different aromatic rings, taking advantage of the Biginelli reaction which includes the reaction of 3-acetyl coumarin with suitable
Unexpected transformations of 3-(bromoacetyl)coumarin provides new evidence for the mechanism of thiol mediated dehalogenation of α-halocarbonyls
Magwenzi, Faith N.,Khanye, Setshaba D.,Veale, Clinton G.L.
, p. 968 - 972 (2017)
The mechanism for the thiol mediated dehalogenation of α-halogenated carbonyls has remained an unresolved problem, despite its ongoing application in synthetic organic chemistry. Nakamura and co-workers first proposed that net dehalogenation occurs via sequential nucleophilic substitutions, while Israel and co-workers concluded that the rate at which dehalogenation occurred suggested that dehalogenation proceeds in a single concerted step. In this study, we investigated the debromination and nucleophilic substitution of 3-(bromoacetyl)coumarin with a variety of thiophenols, whose electron donating or withdrawing natures resulted in large variations in the degree of nucleophilic substitution and dehalogenation products, respectively. Results from these experiments, in addition to an unexpected formation of thioether containing dibenzo[b,d]pyran-6-ones from a Robinson annulation, has provided new evidence for this disputed mechanism.
Dual-function fluorescent probe with red emission for sensing viscosity and OCl? and its applications in bioimaging
Cui, Yali,Jiang, Yingxia,Sun, Xiaodong,Wang, Ruijie,Yan, Fanyong,Zhang, Yuyang
, (2020)
The microenvironment in biological systems is associated with pathological of organisms. In this work, HBTC, a red-emitting probe with abilities of responding to OCl? and environmental viscosity was designed and synthesized to preliminary apply
Design, synthesis and computational studies involving Indole-Coumarin hybrids as galectin-1 inhibitors
Sethi, Aaftaab,Sasikala,Jakkula, Pranay,Gadde, Divya,Sanam, Swetha,Qureshi, Insaf A.,Talla, Venu,Alvala, Mallika
, p. 2791 - 2805 (2021)
In continuation of our quest to develop non-carbohydrate galectin-1 inhibitors, we have designed and synthesized 20 indole-coumarin hybrids linked via chalcone. Compounds 6i and 7e were found to decrease galectin-1 levels significantly in galectin-1 enzyme assay at 20?μM concentration. Binding affinity studies carried out by fluorescence spectroscopy revealed that 6i binds to galectin-1 with a binding constant (Ka) value of 5.4 × 105?M?1 while 7e was found to have a slightly higher affinity than 6i with Ka of 6.6 × 105?M?1. Molecular docking was carried out to ascertain the interaction between ligand and protein. To further gain structural insights into the binding of the compounds, 30?ns molecular dynamic simulations were carried out. The studies revealed that compound 7e was stable within the subsite C of galectin carbohydrate recognition domain while 6i fluctuated throughout the simulation. In addition, 7e maintained continuous interaction with Trp68 and His52, the two key amino acid residues are responsible for recognition of ligands within the active site. Furthermore, 7e displayed H-bond interactions with highly conserved amino acids within galectin-1 CRD, i.e., Arg48, Asn61 and Glu71. Free energy of binding evaluated by MM-GBSA calculations was also in accordance with experimental data. 7e was calculated to have binding energy of ??53.40?kcal/mole while 6i was found to have a value of ??45.63?kcal/mole. Graphical abstract: [Figure not available: see fulltext.]
Synthesis and antibacterial activity of Zn(II) Schiff base complexes derived from 3-acetyl-2H-chromen-2-one
Hussain, Habib,Gilani, Syeda Rubina,Jabeen, Farkhanda,Ali, Zulfiqar,Rehman, Hajira,Hussain, Imdad
, p. 3440 - 3444 (2015)
Zn(II) Schiff base complexes viz., bis[(E)-3-(1-(p-tolylimino)ethyl)-2H-chromen-2-one]zinc(II), bis[(E)-3-(1-((4-chlorophenyl)- imino)ethyl)-2H-chromen-2-one]zinc(II) and bis[(E)-3-(1-((2-nitrophenyl)imino)-ethyl)-2H-chromen-2-one]zinc(II) derived from 3-
A self-assembled π-conjugated system as an anti-proliferative agent in prostate cancer cells and a probe for intra-cellular imaging
Lalitha, Krishnamoorthy,Jenifer, Preethi,Prasad, Y. Siva,Muthusamy, Kumarasamy,John, George,Nagarajan, Subbiah
, p. 48433 - 48437 (2014)
Multifunctional π-conjugated systems derived from renewable resource that self-assemble into supramolecular structures are reported. The aggregation of compounds in different solvents strongly influences their optical properties. These π-conjugated molecules can be used for live cell imaging applications. They also show low cytotoxicity in fibroblasts and suppress proliferation in PC3 prostate cancer cells.
Zn2+ specific colorimetric receptor based on coumarin
Upadhyay, Kaushal Kumar,Mishra, Rakesh Kumar
, p. 1211 - 1215 (2010)
The receptor 1 having coumarin and thiazole as electron-deficient and-rich centers respectively acted as a colorimetric receptor selectively for Zn 2+ as its chloride salt in DMSO/aq. DMSO (10:90 v/v) by exhibiting a remarkable bathochromic shifting of 120 nm in its 375 nm UV-visible absorption band. The interaction of receptor 1 with a number of metal ions ranging from s,p to d blocks as their chloride salts indicated the selectivity of the same toward Zn2+. Transmission electron microscopy (TEM) along with spectroscopic studies indicated Zn2+ triggered aggregate formation of the receptor 1 as the key step toward sensing.
An approach for continuous-flow processing of reactions that involve the in situ formation of organic products
Kelly, Christopher B.,Lee, Christopher,Leadbeater, Nicholas E.
, p. 263 - 265 (2011)
A simple adaptation allows batch protocols developed using microwave heating that involve formation of solid organic products to be scaled up using conventionally-heated flow chemistry with minimal or no re-optimization or modification. The product stream is intercepted with a flow of a suitable organic solvent upon exiting the heated zone, this solubilizing the product and allowing it to pass through the back-pressure regulator without aggregation of particulate material.
Strongly fluorescent organogels and self-assembled nanostructures from pyrene coupled coumarin derivatives: Application in cell imaging
Lalitha, Krishnamoorthy,Nagarajan, Subbiah
, p. 5690 - 5701 (2015)
Three different coumarin coupled pyrene derivatives with varying hydrophobic units (alkyl chains) have been synthesised and well characterized using NMR and mass spectral analysis. The gelation behaviour and self-aggregation properties of these compounds were studied relative to the molecular structure and solvent affinity. Among these derivatives, the one which is not having any hydrophobic tail displays efficient gelation in higher alcohols such as decanol and dodecanol. However the other derivatives having saturated and unsaturated hydrophobic tails form weak gel in different solvents. The morphology of gel was investigated by optical microscopy and high resolution transmission electron microscopy (HRTEM). The investigation of absorption and emission spectra of these compounds revealed that the photo-physical properties were significantly influenced by the self-assembly process in different solvents. The concentration dependent emission and 1H NMR studies clearly suggest that the π-π stacking interaction and hydrogen bonding between carbonyl groups of coumarin coupled pyrene with the -OH group of solvent were the driving forces for the process of gelation and self-aggregation. Rheological investigation clearly demonstrates the flow behaviour and reversible nature of organogel under temperature and strain ramp up and ramp down experimental conditions. By getting clue from the self-assembly mechanism in different solvents, we derived nano-flakes from coumarin coupled pyrene derivatives and further explored their potential applications in the field of cell imaging. The size of the self-aggregated particles in the DMSO-water mixture has been identified using HRTEM and a zetasizer. The nanomaterials obtained via the self-assembly process were used for fibroblast and PC3 prostate cancer cell imaging applications. Further investigation reveals that these compounds suppress the proliferation of PC3 cells.
