- A regioselective synthesis of novel functionalized organochalcogen compounds by chalcogenocyclofunctionalization reactions based on Chalcogen halides and natural products
-
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.
-
supporting information
(2021/07/22)
-
- Synthesis of Functional Dihydro-1,4-benzoxaselenines from Carvacrol Allyl Ether and Selenium Dihalides
-
Abstract: One-step procedures have been developed for the selective synthesis of functionalized 2,3-dihydro-1,4-benzoxaselenines in 90–98% yields by cyclization of carvacrol allyl ether with selenium dihalides. Annulation/acetoxyselenation reaction has be
- Musalov,Yakimov,Potapov,Amosova
-
p. 2258 - 2262
(2021/02/09)
-
- Synthesis and biological evaluation of carvacrol-based derivatives as dual inhibitors of H. Pylori strains and ags cell proliferation
-
This study reports on the synthesis, structural assessment, microbiological screening against several strains of H. pylori and antiproliferative activity against human gastric adenocarcinoma (AGS) cells of a large series of carvacrol-based compounds. Structural analyses consisted of elemental analysis,1 H/13 C/19 F NMR spectra and crystallographic studies. The structure-activity relationships evidenced that among ether derivatives the substitution with specific electron-withdrawing groups (CF3 and NO2) especially in the para position of the benzyl ring led to an improvement of the antimicrobial activity, whereas electron-donating groups on the benzyl ring and ethereal alkyl chains were not tolerated with respect to the parent compound (MIC/MBC = 64/64 μg/mL). Ester derivatives (coumarin-carvacrol hybrids) displayed a slight enhancement of the inhibitory activity up to MIC values of 8–16 μg/mL. The most interesting compounds exhibiting the lowest MIC/MBC activity against H. pylori (among others, compounds 16 and 39 endowed with MIC/MBC values ranging between 2/2 to 32/32 μg/mL against all the evaluated strains) were also assayed for their ability to reduce AGS cell growth with respect to 5-Fluorouracil. Some derivatives can be regarded as new lead compounds able to reduce H. pylori growth and to counteract the proliferation of AGS cells, both contributing to the occurrence of gastric cancer.
- Sisto, Francesca,Carradori, Simone,Guglielmi, Paolo,Traversi, Carmen Beatrice,Spano, Mattia,Sobolev, Anatoly P.,Secci, Daniela,Di Marcantonio, Maria Carmela,Haloci, Entela,Grande, Rossella,Mincione, Gabriella
-
-
- Semisynthetic Phenol Derivatives Obtained from Natural Phenols: Antimicrobial Activity and Molecular Properties
-
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
-
p. 323 - 330
(2018/01/17)
-
- Regioselective iron-catalyzed decarboxylative allylic etherification
-
[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.
-
supporting information; experimental part
p. 5650 - 5652
(2010/02/28)
-
- Solid-supported synthesis of bio-active carvacrol compounds using microwaves
-
The most abundant and potent natural products having a broad spectrum of biological activity against various pests are terpenoids, especially monoterpenoids. The chemical modification of natural monoterpenoids has been reported to result in modified biological activity. The present work emphasizes the structural modification of carvacrol, a phenolic monoterpenoid, through the synthesis of different ether and ester derivatives that are useful for structure-activity relationship studies to exploit the potent molecules. The carvacrol was reacted with alkyl halides and acid chlorides under microwaves using solid supports such as silica gel, alumina, and fly ash to give ethers and esters, respectively. The synthesis of dimeric ether and ester compounds using dihalides and acid dichlorides was conducted with novel reactions. Additional features of the methodology include very fast reactions, higher yields and purities of the products, and an ecofriendly approach. Copyright Taylor & Francis Group, LLC.
- Narkhede,More,Dalal,Mahulikar
-
p. 2413 - 2418
(2008/09/21)
-