65591-12-0Relevant academic research and scientific papers
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 derived immunomodulatory molecules against visceral leishmaniasis
Charan Raja, Mamilla R.,Velappan, Anand Babu,Chellappan, Davidraj,Debnath, Joy,Kar Mahapatra, Santanu
, p. 503 - 518 (2017/08/22)
Visceral leishmaniasis (VL) is a life threatening infectious disease caused by Leishmania donovani. It leads to the severe immune suppression in the host defense system. Higher cytotoxicity, rigorous side effects and lower therapeutic indexes (TI) of current antileishmanial drugs have created a necessity to develop new molecules with better antileishmanial activity and high TI value. In this study, we have synthesized 36 derivatives of eugenol and screened them for their activity against promastigote and amastigote forms of L. donovani. Among the synthesized derivatives, comp.35 showed better antileishmanial activity against extra cellular promastigotes (IC50- 20.13 ± 0.91 μM) and intracellular amastigotes (EC50-4.25 ± 0.26 μM). The TI value (82.24 ± 3.77) was found to improve by 10–13 fold compared to Amphotericin B and Miltefosine respectively. Treatment with comp.35 (5 μg/ml) enhanced the nitric oxide (NO) generation, iNOS2 mRNA expression (～8 folds increase) and decreased the arginase-1 activity (～4 folds) in L. donovani infected peritoneal macrophages. Comp.35 had also increased the IL-12 (～6 folds) and decreased the IL-10 (～3 folds) mRNA expression and release in vitro. Results of in vivo studies revealed that comp.35 treatment at 25 mg/kg body weight efficiently cleared the hepatic and splenic parasite burden with enhanced Th1 response in L. donovani infected BALB/c mice. Hence, this study clearly represents comp.35, as an immunomodulatory molecule, can induce host protective immune response against visceral leishmaniasis through enhanced NO generation and Th1 response, which are essentials against this deadly disease.
Synthesis and antibacterial study of eugenol derivatives
Abdul Rahim, Nurul Hazwani Che,Asari, Asnuzilawati,Ismail, Noraznawati,Osman, Hasnah
, p. 22 - 26 (2016/12/22)
A series of eugenol derivatives (2-14) were synthesized and evaluated for their antibacterial activity against five bacterial test strains; three Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus and Staphylococcus epidermidis) and two Gram-negative bacteria (Escherichia coli and Salmonella typhimurium) using well-diffusion method. Among the compounds tested, compounds 2-4 displayed susceptible activity toward S. epidermidis with 16-18 mm whereas compounds 12 exhibited susceptible inhibition towards S. aureus only with inhibition diameter of 16 mm, respectively. Other compounds possessed varied antibacterial activities classified as intermediate or resistance indicating that eugenol derivatives have narrow spectrum activity and specifically to Gram-positive bacteria.
Eugenol fatty acid ester derivative as well as application and preparation method thereof
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Paragraph 0044-0045, (2017/11/18)
The invention discloses a eugenol fatty acid ester derivative as well as application and a preparation method thereof. Eugenol fatty acid ester is obtained by an esterification reaction of eugenol and straight-chain fatty acid. The method comprises the following steps: firstly, preparing acyl chlorine by reacting fatty acid with thionyl chloride; mixing eugenol with an equal mole amount of pyridine or triethylamine; then, dropwise adding the prepared acyl chloride under the cooling action of an ice bath to generate the eugenol fatty acid ester. Eugenol ester can be applied to external preparations such as patches, cataplasm, ointments, gels and spray agents as a penetration enhancer in order to increase the transdermal absorption amount of medicaments, is a very good percutaneous absorption penetration enhancer, and has a wide application prospect.
Antimicrobial and cytotoxic evaluation of eugenol derivatives
Martins, Rosiane Mastelari,Farias, Marília D’ Avila,Nedel, Fernanda,de Pereira, Claudio M. P.,Lencina, Claiton,Lund, Rafael Guerra
, p. 2360 - 2367 (2016/10/25)
Eugenol is the major phenolic component of clove essential oil and it has been used in medical and dental practice for its properties like analgesic, local anesthetic, and antioxidant. It is known that eugenol can denature proteins and react with cell membrane phospholipids changing their permeability and inhibiting a great number of Gram-negative and Gram-positive bacteria as well as different types of yeast. Eugenol has ever demonstrated antimicrobial properties; thus, the search for the optimization through structural changes appears to be interesting for the development of new antimicrobials. This study aimed to evaluate the antimicrobial activity and cytotoxic characteristics of eugenol analogs. From natural eugenol, 14 derivatives were obtained by typical acylation and alkylation. Their antimicrobial activity was evaluated by the broth microdilution method. The compounds were assessed against Staphylococcus aureus ATCC 19095, Enterococcus faecalis ATCC 4083, Escherichia coli ATCC29214, Pseudomonas aeruginosa ATCC 9027, Candida albicans ATCC 62342 and the following clinical isolates from the human oral cavity: C. albicans (3), C. parapsilosis C. glabrata C. lipolytica, and C. famata. Cytotoxicity against mouse embryonic fibroblast (NIH/3T3) cell line was evaluated by MTT colorimetric assay. The majority of compounds demonstrated significant antimicrobial activities. In general, the compounds presented very low or no cytotoxicity, with an inhibitory ratio lower than 50 % against NIH/3T3 cell line.
Isomerizing ethenolysis as an efficient strategy for styrene synthesis
Baader, Sabrina,Ohlmann, Dominik M.,Goossen, Lukas J.
supporting information, p. 9807 - 9810 (2013/08/23)
A shrinking chain: A bimetallic system consisting of [{Pd(μ-Br)(tBu 3P)}2] and a ruthenium metathesis catalyst has been found to efficiently promote the cross-metathesis between substituted alkenes and ethylene, while continuously migrating the double bond along the alkenyl chain (see scheme). When alkenylarenes, such as the natural products eugenol, safrol, or estragol, were treated with this catalyst under an ethylene atmosphere, they were cleanly converted into the corresponding styrenes and propylene gas. Copyright
