53940-49-1Relevant articles and documents
Novel propanolamine derivatives attached to 2-metoxifenol moiety: Synthesis, characterization, biological properties, and molecular docking studies
Ergon, Derya,Genc Bilgicli, Hayriye,Taslimi, Parham,Zengin, Mustafa,Akyaz? Kuru, ?nci,Gül?in, ?lhami,Tüzün, Burak
, (2020)
The synthesis of seven new ?-amino alcohols was designed and performed by starting from eugenol, a natural phenolic compound known to be biologically active. The synthesized compounds were obtained in yields ranging from 54 to 81%. Molecule structures were determined with FT-IR, 1H NMR and 13C NMR spectroscopies. In addition, the inhibitory effects of these substances on acetylcholinesterase (AChE), α-glycosidase (α-Gly), human carbonic anhydrase I (hCA I), and human carbonic anhydrase II (hCA II) enzymes have been investigated. It has been seen that all compounds have a better ability to inhibit compared to existing tried inhibitors. Among these, the best inhibitor against AChE enzyme is 2b (Ki 62.08 ± 11.67 μM and IC50 90.33), and against α-Gly, 2c showed the highest effect (Ki 0.33 ± 0.08 μM and IC50 0.28). The best inhibitor against hCA I, and hCA II enzymes is compound 2f. For hCA I and hCA II, Ki value was measured as 9.68 ± 1.32 and 11.46 ± 2.64 μM and IC50 values as 7.37 and 8.26 μM respectively. The interactions of the studied new propanolamine derivatives with the enzymes were done by molecular docking calculations and their biological activities were compared to the experimental tests. Studied enzymes in molecular docking calculations are acetylcholinesterase (AChE) is PDB ID: 4M0E, α-glycosidase (α-Gly) is PDB ID: 1R47, human carbonic anhydrase isoenzyme I (hCA I) PDB ID: 3LXE is human carbonic anhydrase isoenzyme II (hCA II) is PDB ID: 5 AML.
[Zinc(II)(Pyridine-Containing Ligand)] Complexes as Single-Component Efficient Catalyst for Chemical Fixation of CO2 with Epoxides
Abbiati, Giorgio,Caselli, Alessandro,Cavalleri, Matteo,Panza, Nicola,Rizzato, Silvia,Tseberlidis, Giorgio,di Biase, Armando
supporting information, p. 2764 - 2771 (2021/06/25)
The reaction between epoxides and CO2 to yield cyclic carbonates is efficiently promoted under solvent-free and relatively mild reaction conditions (0.5 mol % catalyst loading, 0.8 MPa, 125 °C) by zinc(II) complexes of pyridine containing macrocyclic ligands (Pc?L pyridinophanes). The zinc complexes have been fully characterized, including X-ray structural determination. The [Zn(II)X(Pc?L)]X complexes showed good solubility in several polar solvents, including cyclic carbonates. The scope of the reaction under solvent-free conditions has been studied and good to quantitative conversions with excellent selectivities have been obtained, starting from terminal epoxides. When solvent-free conditions were not possible (solid epoxides or low solubility of the catalyst in the oxirane) the use of cyclic carbonates as solvents has been successfully investigated. The remarkable stability of the catalytic system has been demonstrated by a series of consecutive runs.
Synthesis of four eugenol metabolites
Jia, Xixi,Li, Jianyong,Liu, Xiwang,Zhou, Hao
supporting information, p. 415 - 418 (2021/09/07)
Four eugenol metabolites were concisely synthesized and their structures were confirmed by1H-NMR,13C-NMR and high-resolution mass (HR-MS). Among them, the synthesis of eugenol-β-D-glucuronide (3) and eugenol sulfate (4) was reported for the first time. The successful synthesis of the four eugenol metabolites provides a material basis for further metabolic study of prodrug aspirin euge-nol ester (AEE).
Amino alcohols from eugenol as potential semisynthetic insecticides: Chemical, biological, and computational insights
Castanheira, Elisabete M. S.,Fernandes, Maria José G.,Gil Fortes, A.,Gon?alves, M. Sameiro T.,Pereira, David M.,Pereira, Renato B.,Pinto, Nuno F. S.,Rodrigues, Ana Rita O.,Sousa, Sérgio F.,Vieira, Tatiana F.
, (2021/11/08)
A series of β-amino alcohols were prepared by the reaction of eugenol epoxide with aliphatic and aromatic amine nucleophiles. The synthesized compounds were fully characterized and evaluated as potential insecticides through the assessment of their biological activity against Sf9 insect cells, compared with a commercial synthetic pesticide (chlorpyrifos, CHPY). Three derivatives bearing a terminal benzene ring, either substituted or unsubstituted, were identified as the most potent molecules, two of them displaying higher toxicity to insect cells than CHPY. In addition, the most promising molecules were able to increase the activity of serine proteases (caspases) pivotal to apoptosis and were more toxic to insect cells than human cells. Structure-based inverted virtual screening and molecular dynamics simulations demonstrate that these molecules likely target acetylcholinesterase and/or the insect odorant-binding proteins and are able to form stable complexes with these proteins. Encapsulation assays in liposomes of DMPG and DPPC/DMPG (1:1) were performed for the most active compound, and high encapsulation efficiencies were obtained. A thermosensitive formulation was achieved with the compound release being more efficient at higher temperatures.
NOVEL 1-PHENYLMONO- OR -POLYHYDROXYPROPANE COMPOUNDS, COMPOSITIONS AND COSMETIC USES THEREOF
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Page/Page column 26; 27; 31, (2017/04/04)
The present invention relates to novel compounds of formula (I) to compositions comprising same, and also to the use thereof for preventing and/or cosmetically treating the signs of aging of the skin.
Oxidation reactions of some natural volatile aromatic compounds: Anethole and eugenol
Elgendy,Khayyat
experimental part, p. 823 - 829 (2009/07/05)
trans-Anethole [1-methoxy-4-(trans-prop-1-en-1-yl)benzene] was isolated from anise seed oil (Pimpinella anisum). Its photochemical oxidation with hydrogen peroxide gave the corresponding epoxy derivative together with 4-methoxybenzaldehyde. The thermal oxidation of trans-anethole with 3-chloroperoxybenzoic acid at room temperature resulted in the formation of dimeric epoxide, 2,5-bis(4-methoxyphenyl)-3,6-dimethyl-1,4-dioxane, as the only product. Photochemical oxygenation of trans-anethole in the presence of tetraphenylporphyrin, Rose Bengal, or chlorophyll as sensitizer led to a mixture of 1-(4-methoxyphenyl)prop-2-en-1-yl hydroperoxide and 4-methoxybenzaldehyde. Eugenol was isolated from clove oil [Eugenia caryophyllus (Spreng.)]. It was converted into 2-methoxy-4-(prop-2-en-1-yl)phenyl hydroperoxide by oxidation with hydrogen peroxide under irradiation. Thermal oxidation of eugenol with 3-chloroperoxypenzoic acid at room temperature produced 2-methoxy-4-(oxiran-2- ylmethyl)phenol, while sensitized photochemical oxygenation (in the presence of Rose Bengal or chlorophyll) gave 4-hydroperoxy-2-methoxy-4-(prop-2-en-1-yl) cyclohexa-2,5-dien-1-one.
Antioxidative phenylpropanoids from berries of Pimenta dioica
Kikuzaki, Hiroe,Hara, Sanae,Kawai, Yayoi,Nakatani, Nobuji
, p. 1307 - 1312 (2007/10/03)
A phenylpropanoid, threo-3-chloro-1-(4-hydroxy-3-methoxyphenyl)propane- 1,2-diol, was isolated from the berries of Pimenta dioica together with five known compounds, eugenol, 4-hydroxy-3-methoxycinnamaldehyde, 3,4- dimethoxycinnamaldehyde, vanillin and 3-(4-hydroxy-3-methoxyphenyl)propane- 1,2-diol. In addition, the stereochemistry of 3-(4-hydroxy-3- methoxyphenyl)propane-1,2-diol was determined. The phenylpropanoids inhibited autoxidation of linoleic acid in a water-alcohol system.
Selective catalyzed-rearrangement of terminal epoxides to methyl ketones
Prandi,Namy,Menoret,Kagan
, p. 449 - 460 (2007/10/02)
Terminal epoxides of the type {A figure is presented} have been selectively converted into methyl ketones by various catalysts. Some lanthanide derivatives, MnI2, and Co2(CO)8 gave the best results. The rearrangement of internal epoxides into ketones is much slower, allowing specific transformation of terminal epoxides. The scope of the reaction and tentative mechanisms are discussed.
