579-60-2Relevant articles and documents
Synthesis and First-Time Assessment of o-Eugenol Derivatives against Mycobacterium tuberculosis
Moraes, Adriana Marques,da Silva, Emerson Teixeira,Wardell, James L.,de Souza, Marcus V. N.
, p. 633 - 638 (2020/07/30)
In this work, we report the first-time assessment of o-eugenol, 6-allyl-2-methoxyphenol, and their selected derivatives, against Mycobacterium tuberculosis H37RV, using the MABA susceptibility test. The bromo, nitro, O-alkylated, and reduced derivatives were obtained by standard methods and were characterized by spectroscopic and mass spectral data. Structure–activity relationships were investigated, with the most active derivatives being 4,5-dibromo-2-methoxy-6-propylphenol (139 μM) and 2-methoxy-3-nitro-6-propylphenol (237 μM). This study provides important information on the rational design of new lead anti-TB drugs based on o-eugenol derivatives.
Semisynthetic Phenol Derivatives Obtained from Natural Phenols: Antimicrobial Activity and Molecular Properties
Pinheiro, Patrícia Fontes,Menini, Luciana Alves Parreira,Bernardes, Patrícia Campos,Saraiva, Sérgio Henriques,Carneiro, José Walkimar Mesquita,Costa, Adilson Vidal,Arruda, Társila Rodrigues,Lage, Mateus Ribeiro,Gon?alves, Patrícia Martins,Bernardes, Carolina De Oliveira,Alvarenga, Elson Santiago,Menini, Luciano
, p. 323 - 330 (2018/01/17)
Semisynthetic phenol derivatives were obtained from the natural phenols: thymol, carvacrol, eugenol, and guaiacol through catalytic oxychlorination, Williamson synthesis, and aromatic Claisen rearrangement. The compounds characterization was carried out by 1H NMR, 13C NMR, and mass spectrometry. The natural phenols and their semisynthetic derivatives were tested for their antimicrobial activity against the bacteria: Staphylococcus aureus, Escherichia coli, Listeria innocua, Pseudomonas aeruginosa, Salmonella enterica Typhimurium, Salmonella enterica ssp. enterica, and Bacillus cereus. Minimum inhibitory concentration (MIC) and minimal bactericidal concentration (MBC) values were determined using concentrations from 220 to 3.44 μg mL-1. Most of the tested compounds presented MIC values ≤220 μg mL-1 for all the bacteria used in the assays. The molecular properties of the compounds were computed with the PM6 method. Through principle components analysis, the natural phenols and their semisynthetic derivatives with higher antimicrobial potential were grouped.
Eugenol synthesis method
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Paragraph 0042; 0043; 0044; 0045; 0046, (2016/10/08)
The invention belongs to the field of organic synthesis and particularly relates to a eugenol synthesis method. According to the eugenol synthesis method, guaiacol and allyl chloride are used as raw materials and are subjected to a catalytic reaction through a catalyst THLD to generate eugenol; an experiment testifies that the eugenol is synthesized by using the novel composite catalyst THLD, so that the conversion rate of the guaiacol and the yield of the eugenol are greatly improved, the conversion rate of the guaiacol reaches to 98 percent and the yield of the eugenol reaches to 88 percent.