61114-24-7Relevant articles and documents
Synthesis of eugenol derivatives and its anti-inflammatory activity against skin inflammation
Agarwal, Karishma,Ahmad, Ateeque,Bawankule, Dnyaneshwar Umrao,Gupta, Amit Chand,Maurya, Anil Kumar,Nooreen, Zulfa,Saxena, Archana,Tandon, Sudeep
, p. 251 - 260 (2019/01/04)
Eugenol is a phytochemical present in aromatic plants has generated considerable interest in the pharmaceutical industries mainly in cosmetics. A series of eugenol esters (ST1-ST7) and chloro eugenol (ST8) have been synthesized. The structures of newly synthesized compounds were confirmed by 1H and 13C NMR and mass spectrometry. In an effort to evaluate the pharmacological activity of eugenol derivatives, we explored its anti-inflammatory potential against skin inflammation using in-vitro and in-vivo bioassay. Synthesized derivatives significantly inhibited the production of pro-inflammatory cytokines against LPS-induced inflammation in macrophages. Among all derivatives, ST8 [Chloroeugenol (6-chloro, 2-methoxy-4-(prop-2-en-1-yl)-phenol)] exhibited most potent anti-inflammatory activity without any cytotoxic effect. We have further evaluated the efficacy and safety in in-vivo condition. ST8 exhibited significant anti-inflammatory activity against TPA-induced skin inflammation without any skin irritation effect on experimental animals. These findings suggested that ST8 may be a useful therapeutic candidate for the treatment of skin inflammation.
Synthesis, antimicrobial activity and in silico studies on eugenol eters
Lazarevi?, Jelena,Kolarevi?, Ana,Stojanovi?, Gordana,?melcerovi?, Andrija,Ciuffreda, Pierangela,Santaniello, Enzo
, p. 801 - 810 (2019/02/15)
The results presented herein represent our continued study based on the modification of phenolic functionality in molecules originated from natural sources by acylation. A small focused library of nineteen eugenyl esters, with four of which are new compounds, is reported. All compounds were subjected to in vitro antimicrobial testing. In silico studies were carried out calculating physico-chemical, pharmacokinetic and toxicological properties, providing more data as additional guidance for further research.
Eugenol derivatives as potential anti-oxidants: Is phenolic hydroxyl necessary to obtain an effect?
D'Avila Farias, Marilia,Oliveira, Pathise Souto,Dutra, Filipe S. Pereira,Fernandes, Thiely Jacobsen,De Pereira, Claudio M. P.,De Oliveira, Simone Quintana,Stefanello, Francieli Moro,Lencina, Claiton Leonetti,Barschak, Alethea Gatto
, p. 733 - 746 (2014/05/06)
Objectives Eugenol, obtained from clove oil (Eugenia caryophyllata), possess several biological activities. It is anti-inflammatory, analgesic, anaesthesic, antipyretic, antiplatelet, anti-anaphylactic, anticonvulsant, anti-oxidant, antibacterial, antidepressant, antifungal and antiviral. The anti-oxidant activity of eugenol have already been proven. From this perspective testing, a series of planned structural derivatives of eugenol were screened to perform structural optimization and consequent increase of the potency of these biological activities. Methods In an attempt to increase structural variability, 16 compounds were synthesized by acylation and alkylation of the phenolic hydroxyl group. Anti-oxidant activity capacity was based on the capture of DPPH radical (2,2-diphenyl-1-picryl-hydrazyl), ABTS radical 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid), measure of TBARS (thiobarbituric acid-reactive species), total sulfhydryl and carbonyl content (eugenol derivatives final concentrations range from 50 to 200 μm). Key findings Four derivatives presented an efficient concentration to decrease 50% of the DPPH radical (EC50) 100 μm, which has a good potential as a free-radical scavenger. Three of these compounds also showed reduction of ABTS radical. Eugenol derivatives presenting alkyl or aryl (alkylic or arylic) groups substituting hydroxyl 1 of eugenol were effective in reducing lipid peroxidation, protein oxidative damage by carbonyl formation and increase total thiol content in cerebral cortex homogenates. In liver, the eugenol derivatives evaluated had no effect. Conclusions Our results suggest that these molecules are promising anti-oxidants agents.
A general route for the stereoselective synthesis of (E)-(1-propenyl)phenyl esters by catalytic CC bond isomerization
Díaz-álvarez, Alba E.,Crochet, Pascale,Cadierno, Victorio
experimental part, p. 2611 - 2620 (2012/05/20)
A general and efficient procedure for the stereoselective synthesis of (E)-(1-propenyl)phenyl esters from readily accessible allylphenols has been developed. The process involves a two-step sequence consisting of the initial acylation of the allylphenols with an acid chloride, followed by catalytic CC bond isomerization in the resulting allylphenyl esters. The latter step was performed in methanol at 80 °C using catalytic amounts (0.5 mol %) of the commercially available bis(allyl)-ruthenium(IV) dimer [{RuCl(μ-Cl) (η3:η3-C10H16)} 2] (C10H16=2,7-dimethylocta-2,6-diene-1,8-diyl) . Reactions proceeded in high yields (68-93%) and short times (4-9 h) with complete E-selectivity.
