Synthesis and pharmacological activity of O-aminoalkyl derivatives of 7-hydroxycoumarin

Konc, Joanna Trykowska; Hejchman, Elżbieta; Kruszewska, Hanna; Wolska, Irena; Maciejewska, Dorota

doi:10.1016/j.ejmech.2011.03.006

Cited by 31 publications

(10 citation statements)

References 15 publications

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“…Hydrogen H‐B is also present in the 4‐methylcoumarin compounds 14 , 15 , 16 , 17 (see Table ). Their resonances are between δ = 6.10 and 6.13 ppm and are in concordance with values reported in the literature for other 4‐methylcoumarins …”

Section: Resultssupporting

confidence: 90%

Molecular structure, experimental and theoretical¹H and¹³C NMR chemical shift assignment of cyclic and acyclic α,β-unsaturated esters

Buceta

Ruiz

Romanelli

et al. 2013

J. Phys. Org. Chem.

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The experimental 1H and 13C NMR spectra of 13 phenyl cinnamates and four 4‐methylcoumarins were investigated and their chemical shifts assigned on the basis of the two‐dimensional spectra. For the unsubstituted cinnamic acid phenyl ester, optimized molecular structures were calculated at a B3LYP/6‐311++G(d,p) level of theory. 1H and 13C NMR chemical shifts were also calculated with the GIAO method at the B3LYP/6‐311 + G(2d,p) level of theory. The comparison between experimental and calculated NMR chemical shift suggests that the experimental spectra are formed from the superposition spectra of the two lowest energy conformers of the compound in solution. The most stable s‐cis configuration found in our studies is also the conformation adopted for a related phenyl cinnamate in solid state. The experimental results were analyzed in terms of the substituent effects. Copyright © 2013 John Wiley & Sons, Ltd.

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Section: Resultssupporting

confidence: 90%

Molecular structure, experimental and theoretical¹H and¹³C NMR chemical shift assignment of cyclic and acyclic α,β-unsaturated esters

Buceta

Ruiz

Romanelli

et al. 2013

J. Phys. Org. Chem.

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“…Therefore, the development of photosensitive systems with low toxicity will be preferably retained for the design of new initiating systems under mild irradiation conditions. Coumarin and its derivatives form a class of natural compounds that exhibit biological activity, e.g., cytotoxic activity against several human tumor cell lines [6,7], as well as spasmolytic, antiarrhythmic [8], and antioxidant [9] activities. Coumarins are also used in flavoring food and in cosmetic products such as fragrances [10,11].…”

Section: Introductionmentioning

confidence: 99%

“…H NMR (CDCl 3 ) δ: 1.22 (t, 6H, J = 7.1 Hz), 3.44 (q, 4H, J = 7.1 Hz), 4.72 (d, 2H, J = 3.7 Hz), 5.00 (s, 1H),6.54 (d, 1H, J = 2.4 Hz),6.62 (dd, 1H, J = 8.8 Hz, J = 2.4 Hz), 7.30-7.40 (m, 4H), 7.63-7.67 (m, 3H), 7.90 (s, 1H);13 C NMR (CDCl 3 ) δ: 12.5, 21.2, 30.3, 34.2, 44.9, 65.1, 97.2, 108.8, 109.3, 114.7, 123.4, 125.5, 125.81, 125.83, 127.5, 128.3, 128.8, 132.6, 133.9, 135.8, 136.3, 136.9, 140.1, 143.7, 150.5, 151.5, 155.6, 160.5; HRMS (ESI MS) m/z: theor: 405.1399 found: 405.1396 (M + . detected).4.1.5.…”

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confidence: 99%

Mono vs. Difunctional Coumarin as Photoinitiators in Photocomposite Synthesis and 3D Printing

et al. 2020

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This work is devoted to investigate three coumarin derivatives (Coum1, Coum2, and Coum3), proposed as new photoinitiators of polymerization when combined with an additive, i.e., an iodonium salt, and used for the free radical polymerization (FRP) of acrylate monomers under mild irradiation conditions. The different coumarin derivatives can also be employed in three component photoinitiating systems with a Iod/amine (ethyl 4-dimethylaminobenzoate (EDB) or N-phenylglycine (NPG)) couple for FRP upon irradiation with an LED @ 405 nm. These compounds showed excellent photoinitiating abilities, and high polymerization rates and final conversions (FC) were obtained. The originality of this work relies on the comparison of the photoinitiating abilities of monofunctional (Coum1 and Coum2) vs. difunctional (Coum3) compounds. Coum3 is a combined structure of Coum1 and Coum2, leading to a sterically hindered chemical structure with a relatively high molecular weight. As a general rule, a high molecular weight should reduce the migration of initiating molecules and favor photochemical properties such as photobleaching of the final polymer. As attempted, from the efficiency point of view, Coum3 can initiate the FRP, but a low reactivity was observed compared to the monofunctional compound (Coum1 and Coum2). Indeed, to study the photochemical and photophysical properties of these compounds, different parameters were taken into account, e.g., the light absorption and emission properties, steady state photolysis, and fluorescence quenching. To examine these different points, several techniques were used including UV-visible spectroscopy, real-time Fourier Transform Infrared Spectroscopy (RT-FTIR), fluorescence spectroscopy, and cyclic voltammetry. The photochemical mechanism involved in the polymerization process is also detailed. The best coumarins investigated in this work were used for laser writing (3D printing) experiments and also for photocomposite synthesis containing glass fibers.

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“…We have proved the importance of substitution on both phenolic group and ortho -position in the phenolic ring in a series of hydroxycoumarins. Introduction of acetyl group to O -alkyl derivatives of 4-methyl-7-hydroxycoumarin increased cytotoxicity and inhibited the growth of renal cancer 786-0, leukemia HL-60 (TB), leukemia CCRF-CEM, non-small- cell lung cancer HOP-92, and colon cancer HCC-2998 cell lines [ 7 ]. Cyanomethoxy derivatives of 7-hydroxycoumarin have been also shown as promising anti-tumor agents.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted preparation, structural characterization, lipophilicity, and anti-cancer assay of some hydroxycoumarin derivatives

et al. 2014

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A new series of hydroxycoumarin derivatives has been synthesized using conventional synthesis. The syntheses were accelerated by microwave assistance. Yields in both cases were comparable (59–69 %). The structures were established by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry. Five compounds (5-hydroxy-4,7-dimethylcoumarin, 6-acetyl-5-hydroxy-4,7-dimethylcoumarin, 4-(cyanomethoxy)chromen-2-one, 5-(cyanomethoxy)-4,7-dimethylchromen-2-one, and 6-acetyl-5-(cyanomethoxy)-4,7-dimethylchromen-2-one) were assayed for anti-cancer activity. For all presented coumarin derivatives, lipophilicity was measured using reversed-phase TLC in different eluent systems with standardization. In addition, the crystal structure of 6-acetyl-5-hydroxy-4,7-dimethylcoumarin has been solved by X-ray structure analysis of single crystals.Graphical abstract

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Synthesis and pharmacological activity of O-aminoalkyl derivatives of 7-hydroxycoumarin

Cited by 31 publications

References 15 publications

Molecular structure, experimental and theoretical¹H and¹³C NMR chemical shift assignment of cyclic and acyclic α,β-unsaturated esters

Molecular structure, experimental and theoretical¹H and¹³C NMR chemical shift assignment of cyclic and acyclic α,β-unsaturated esters

Mono vs. Difunctional Coumarin as Photoinitiators in Photocomposite Synthesis and 3D Printing

Microwave-assisted preparation, structural characterization, lipophilicity, and anti-cancer assay of some hydroxycoumarin derivatives

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Synthesis and pharmacological activity of O-aminoalkyl derivatives of 7-hydroxycoumarin

Cited by 31 publications

References 15 publications

Molecular structure, experimental and theoretical1H and13C NMR chemical shift assignment of cyclic and acyclic α,β-unsaturated esters

Molecular structure, experimental and theoretical1H and13C NMR chemical shift assignment of cyclic and acyclic α,β-unsaturated esters

Mono vs. Difunctional Coumarin as Photoinitiators in Photocomposite Synthesis and 3D Printing

Microwave-assisted preparation, structural characterization, lipophilicity, and anti-cancer assay of some hydroxycoumarin derivatives

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Molecular structure, experimental and theoretical¹H and¹³C NMR chemical shift assignment of cyclic and acyclic α,β-unsaturated esters

Molecular structure, experimental and theoretical¹H and¹³C NMR chemical shift assignment of cyclic and acyclic α,β-unsaturated esters