2555-37-5Relevant articles and documents
Tosyl cyanide as a C-sulfinylating agent: 3-sulfinylation of 4-hydroxycoumarins and related heterocycles
Akula, Ramulu,Ibrahim, Hasim
, p. 25719 - 25722 (2013)
Treatment of 4-hydroxycoumarins and related heterocycles with TsCN under mild basic reaction conditions produces the corresponding 3-sulfinylated products in high yields. Sulfinyl transfer is proposed to occur from sulfinyl cyanate 1, generated in situ by base-catalysed rearrangement of TsCN.
Coumarin Derivative Directly Coordinated to Lanthanides Acts as an Excellent Antenna for UV-Vis and Near-IR Emission
Guzmán-Méndez, óscar,González, Federico,Bernès, Sylvain,Flores-álamo, Marcos,Ordó?ez-Hernández, Javier,García-Ortega, Héctor,Guerrero, Joselin,Qian, Wenjie,Aliaga-Alcalde, Nuria,Gasque, Laura
, p. 908 - 911 (2018)
A chelating coumarin-derived ligand sensitizes all emitting lanthanide ions in the solid state and gives high absolute quantum yields for ethanol solutions of complexes of Sm, Eu, Tb, and Dy, above 20% for the last two. Crystal structures of these four complexes are [Ln(Cum)3(H2O)(X)]·X where X = MeOH or EtOH.
Proton transfer inhibited charge transfer in a coumarinyl chalcone: Hassle free detection of chloroform vapor in alcohol medium and in neat solution
Bhattacharyya, Arghyadeep,Guchhait, Nikhil
, (2021)
The photophysical aspects of a synthesized coumarinyl chalcone derivative 3-((2E, 4E)-5-(4-(dimethylamino) phenyl) penta-2, 4-dienoyl)-4-hydroxy-2H-chromen-2-one (DPPHC) were explored. DPPHC shows excited state intramolecular proton transfer (ESIPT) suppressed excited state intramolecular charge transfer (ESICT) as evidenced from steady state and time resolved spectroscopic analysis. Interestingly, DPPHC behaves as a strong red emitter solely in chloroform and dichloromethane semi-polar solvents exclusively. Using this property, on-spot detection of these two solvents was achieved in paper strips coated with DPPHC as well as in spiked alcohol samples by emission ratiometry change.
Synthesis, photoluminescent behaviors, and theoretical studies of two novel ketocoumarin derivatives
Li, Jing,Li, Xianggao,Wang, Shirong
, p. 31 - 36 (2012)
Two new coumarin derivatives, 3-[3-(4-formylphenyl)prop-2-enoyl]-coumarin (FEC) and 4-hydroxy-3-[3-(4-formylphenyl)prop-2-enoyl]-coumarin (HFEC), were synthesized and characterized by MS, 1H NMR, FT-IR, and TG. The UV-vis absorption and photoluminescence (PL) of FEC and HFEC were also studied. Results show that the two compounds exhibit high fluorescence quantum yields, large Stokes shifts, and strong blue emissions. The molecular structures, the lowest energy transitions, the resonance frequencies, and the UV-vis spectra of FEC and HFEC were calculated using the density functional theory (DFT) and time-dependent density functional theory (TD-DFT) at the B3LYP/6-31G(d) level.
Benzopyrans. Part 30. Synthesis of substituted xanthones from 3-acyl-2-methyl-1-benzopyran-4-ones
Ghosh, Chandra Kanta,Sahana, Sirin,Patra, Amarendra
, p. 4127 - 4134 (1993)
The xanthone 8 results from the base catalysed self-condensation of the chromone 1. The chromone 2 gives the xanthones 9 and 11 with sodium and DMF-POCl3 respectively, phenol 14 with NaOMe, and the pyran 22 with 2-thiomethylchromone 6. The enamine 16 on Vilsmeier-Haak reaction affords the chloroxanthone 12. The pyran 15, isolated as a byproduct from the reaction of ω-acetyl-2-hydroxyacetophenone with HC(OEt)3-Ac2O, affords the xanthone 13 by refluxing with NaOMe in MeOH.
Synthesis, computational study and cytotoxicity of 4-hydroxycoumarin-derived imines/enamines
Vaseghi, Samaneh,Yousefi, Mohammad,Shokrzadeh, Mohammad,Hossaini, Zinatossadat,Hosseini-khah, Zahra,Emami, Saeed
, p. 1011 - 1024 (2020/05/05)
Abstract: In this study, we applied a direct condensation between 3-acetyl-4-hydroxy-2H-chromen-2-one and different amines (anilines and benzyl amines) in order to synthesize some coumarin-based imines/enamines (3a–o) as cytotoxic agents. All the compounds were characterized by means of FT-IR, NMR, mass spectroscopy and elemental analyses. Since the title compounds can exist as different forms including (s-cis)-imine and (s-trans)-imine or (E and Z)-enamines, their conformational and geometrical aspects were investigated computationally by DFT method. The optimized geometry parameters, ΔE, ΔG, ΔH, Mulliken atomic charge, HOMO and LUMO energy, and NBO analysis suggested that these compounds can exist predominantly in (E)-enamine form. All the synthesized compounds (3a–o) were evaluated in vitro for their cytotoxic activities against cancer cell lines (MCF-7 and A549) and normal cell line (BEAS-2B) using the MTT assay. The 4-hydroxybenzyl derivative 3k was found to be the most potent cytotoxic agent with no selectivity, similar to doxorubicin. However, the 4-chlorobenzyl analog 3o could be considered as an equipotent compound respect to doxorubicin with higher selectivity. Graphic abstract: [Figure not available: see fulltext.].
Angiokinase inhibition of VEGFR-2, PDGFR and FGFR and cell growth inhibition in lung cancer: Design, synthesis, biological evaluation and molecular docking of novel azaheterocyclic coumarin derivatives
Abd Elaziz, Moaaz R.,Abdelrahman, Basel A.,Abdou, Andrew M.,Ahmed, Eman Y.,El-Mansy, Mohamed F.,Elsayed, Kenzi H.,Elserwy, Weam S.,Salem, Abdelrahman M.,Serry, Aya M.
, (2021/07/14)
The present work represents the design and synthesis of some azaheterocyclic coumarin derivatives which are evaluated as anti-lung cancer agents. Ten out of the twenty azaheterocyclic compounds showed superior activity than the standard drug staurosporine against non-small cell lung cancer (A549). Representing the four different azaheterocyclic series, compounds 4a, 5d, 6e, and 7d, which demonstrated IC50s of 2.38, 2.39, 1.05 and 3.98 μM, respectively, each exhibiting the best cytotoxicity in its group, were selected for further assessment of their toxicity on normal lung cells (WI-38). Compound 4a was selected for further investigations because it remarkably revealed less cytotoxicity (IC50 = 53.76 μM) than 7d (IC50 = 19.95 μM) on (WI-38) compared to staurosporine (IC50 = 24.41 μM). 4a was assessed for its ability to inhibit the angiokinases VEGFR-2, PDGFR, FGFR and the growth factor EGFR, remarkably it showed better VEGFR-2, PDGFR, FGFR inhibition than the reference drugs used and exhibited as well noticeable EGFR inhibition. Going further, 4a was capable of arresting the cell cycle at pre-G1 phase and S phase and inducing apoptosis. Moreover, the capability of the target 4a to interact with the key amino acids of VEGFR-2 binding site was detected by molecular docking. Finally, the in silico physicochemical properties of 4a were studied.