- A regioselective synthesis of novel functionalized organochalcogen compounds by chalcogenocyclofunctionalization reactions based on Chalcogen halides and natural products
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The regioselective synthesis of novel functionalized condensed organochalcogen compounds by chalcogenocyclofunctionalization reactions based on chalcogen halides and the natural products thymol and carvacrol has been developed. The reactions of selenium d
- Amosova, Svetlana V.,Maylyan, Arkady A.,Musalov, Maxim V.,Musalova, Maria V.,Potapov, Vladimir A.,Yakimov, Vladimir A.,Zinchenko, Sergey V.
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supporting information
(2021/07/22)
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- Semisynthetic Phenol Derivatives Obtained from Natural Phenols: Antimicrobial Activity and Molecular Properties
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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.
- 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
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p. 323 - 330
(2018/01/17)
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- Synthesis and bio-evaluation of human macrophage migration inhibitory factor inhibitor to develop anti-inflammatory agent
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Macrophage migration inhibitory factor (MIF), a pro-inflammatory cytokine, is involved in the development of an array of inflammatory disorders including rheumatoid arthritis, inflammatory bowel disease, psoriasis, multiple sclerosis and sepsis. The synthesis of MIF-inhibitor is a rationale approach to develop novel anti-inflammatory agent to treat multitude of inflammatory diseases. In this work, we have synthesized and evaluated MIF-inhibitory activity of a series of small molecules containing isoxazoline skeleton. Mode of binding of this inhibitor to human MIF (huMIF) was determined by docking studies. The synthesized molecules inhibit tautomerase activity of huMIF. The anti-inflammatory activity of the most active inhibitor, 4-((3-(4-hydroxy-3- methoxyphenyl)-4, 5-dihydroisoxazol-5-yl) methoxy) benzaldehyde (4b) was evaluated against huMIF-induced inflammation in a cellular model (RAW 264.7 cell). Compound 4b significantly inhibits huMIF-mediated NF-κB translocation to the nucleus, up-regulation of inducible nitric oxide synthase and nitric oxide production in RAW 264.7 cell which are the markers for inflammation. The compound 4b is not cytotoxic as evident from cell viability assay. Hence, the compound 4b has potential to be a novel anti-inflammatory agent.
- Alam, Athar,Pal, Chinmay,Goyal, Manish,Kundu, Milan Kumar,Kumar, Rahul,Iqbal, Mohd Shameel,Dey, Sumanta,Bindu, Samik,Sarkar, Souvik,Pal, Uttam,Maiti, Nakul C.,Adhikari, Susanta,Bandyopadhyay, Uday
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body text
p. 7365 - 7373
(2012/01/06)
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- Regioselective iron-catalyzed decarboxylative allylic etherification
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[Chemical Equation Presented] An anionic iron complex catalyzes the decarboxylative allylation of phenols to form allylic ethers in high yield. The allylation is regioselective rather than regiospecific. This suggests that the allylation proceeds through π-allyl iron intermediates in contrast to related allylations of carbon nucleophiles that have been proposed to proceed via π-allyl complexes. Ultimately, iron catalysts have the potential to replace more expensive palladium catalysts that are typically utilized for decarboxylative couplings.
- Trivedi, Rushi,Tunge, Jon A.
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supporting information; experimental part
p. 5650 - 5652
(2010/02/28)
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- Microwave-assisted sinthesis of thymyl ethers and esters in aqueous medium
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Various thymyl ethers and esters have been synthesized by reactions of thymol with alkyl halides and acid chlorides, respectively, in aqueous medium under environmentally benign conditions using microwave irradiation. The products are important as potent pest managing agents.
- More,Pawar,Dewang,Patil,Mahulikar
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p. 217 - 218
(2007/10/03)
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- A new synthesis of benzofurans from phenols via claisen rearrangement and ring-closing metathesis
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Based on Claisen rearrangement, the double bond isomerization of O-allyl function together with the formation of O-vinyl function in one pot, and ring-closing metathesis (RCM), various phenols were transformed into various benzofurans in good yields.
- Tsai, Tzu-Wei,Wang, Eng-Chi,Li, Sie-Rong,Chen, Yung-Hua,Lin, Yu-Li,Wang, You-Feng,Huang, Keng-Shiang
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p. 1307 - 1318
(2007/10/03)
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- The sulfonation of methyl and prenyl ethers of naturally occurring phenols with trimethylsilylchlorosulfonate as sulfonating agent
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At room temperature trimethylsilylchlorosulfonate has been found to be an effective and a mild reagent for the nuclear sulfonation of some methyl and prenyl ethers of naturally occurring phenols.
- Petit, Philippe,Bourgeois, Paul
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p. 194 - 195
(2007/10/03)
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