74368-00-6Relevant academic research and scientific papers
Biotechnological Potential of Eugenol and Thymol Derivatives Against Staphylococcus aureus from Bovine Mastitis
Nunes, Daiana O. S.,Vinturelle, Rafaelle,Martins, Francislene J.,dos Santos, Thiago F.,Valverde, Alessandra Leda,Ribeiro, Carlos Magno R.,Castro, Helena C.,Folly, Evelize
, p. 1846 - 1855 (2021/04/29)
Bovine mastitis is an infectious disease that affects the mammary gland of dairy cattle with considerable economic losses. Staphylococcus aureus is the main microorganism involved in this highly contagious process, and the treatment is only using antibiotics. Currently, the search for new treatment and/or compounds is still in need due to microbial resistance. In this work, we evaluated the potential of eugenol and thymol derivatives against S. aureus strains from bovine mastitis. On that purpose, nine derivatives were synthesized from eugenol and thymol (1–9), and tested against 15 strains of S. aureus from subclinical bovine mastitis. Initially, the strains were evaluated for the biofilm production profile, and those with strong adherence were selected to the antimicrobial sensitivity determination in the Minimum Inhibitory Concentration (MIC) assays. Herein the compounds toxicity was also evaluated by in silico analysis using Osiris DataWarrior software. The results showed that 60% of the strains were considered strongly adherent and three strains (S. aureus 4271, 4745 and 4746) were selected for the MIC tests. Among the nine eugenol and thymol derivatives tested, four were active against the evaluated strains (MIC = 32?μg?mL?1) within CLSI standard values. In silico analysis showed that all derivatives had cLopP ??4 and TPSA 140 ?2, and similar theoretical toxicity parameters to some antibiotics currently on the market. These molecules also showed negative drug-likeness values, pointing to the originality of these structures and theoretical feasibility on escaping of resistance mechanism and act against resistant strains. Thus, these eugenol derivatives may be considered as promising for the development of new treatments against bovine mastitis and future exploring on this purpose.
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 of isoquinoline alkaloid derivatives from eugenol
Mikhailovskii,Surikova,Limanskii,Vakhrin
experimental part, p. 285 - 287 (2012/09/07)
Alkylation under phase-transfer catalysis conditions (18-crown-6/KOH) of eugenol was used for cyclocondensation with nitriles (Ritter reaction), the products of which were isoquinoline derivatives.
Design and synthesis of novel pyrethriods containing eugenol moiety
Wang, Xinlong,Yi, Meigui,Du, Quanhai,Wu, Aimin,Xiao, Rong
, p. 2827 - 2830,4 (2020/07/30)
A novel series of pyrethriods was designed and synthesized by connecting various eugenol derivatives to either a chrysanthematic acid or 2-(4-chlorophenyl)-3-methylbutanoic acid. The insecticidal activity of target compounds has been evaluated by an immersion method on the fourth instar larvae of Culex pipens quinquefasciatus. The results revealed that the larvae were sensitive to synthesized compounds. Varying substituents in both acid moiety and eugenol group resulted in new compounds that exhibited different contact toxicity. Compound 3a showed the highest activity and is currently under further investigation.
Synthesis of novel isoxazolines via 1,3-dipolar cycloaddition and evaluation of anti-stress activity
Maurya, Rakesh,Ahmad, Ausaf,Gupta, Prasoon,Chand, Kailash,Kumar, Manmeet,Jayendra,Rawat, Preeti,Rasheed, Naila,Palit, Gautam
experimental part, p. 139 - 145 (2012/03/10)
We have synthesized a series of novel isoxazolines via 1,3-dipolar cycloaddition of in situ generated nitrile oxide from 2,4-dimethoxy benzaldoxime and naphthaldehyde oxime with 4-allyl-2-methoxyphenol derivatives. The synthesized compounds were evaluated for anti-stress activity in acute stress (AS) induced peripheral changes. Adult male Sprague-Dawley rats, subjected to AS, cause a significant increase in gastric ulceration, adrenal gland weight, plasma glucose, corticosterone levels, and creatine kinase activity. Compounds 3d, 3g, 5b, 5c, 5d, and 5g displayed most promising anti-stress effect by reverting these peripheral stress parameters at a dose of 40 mg/kg p.o.
