65211-53-2Relevant academic research and scientific papers
Natural-Product-Inspired Aminoepoxybenzoquinones Kill Members of the Gram-Negative Pathogen Salmonella by Attenuating Cellular Stress Response
Mandl, Franziska A.,Kirsch, Volker C.,Ugur, Ilke,Kunold, Elena,Vomacka, Jan,Fetzer, Christian,Schneider, Sabine,Richter, Klaus,Fuchs, Thilo M.,Antes, Iris,Sieber, Stephan A.
, p. 14852 - 14857 (2016/11/23)
Gram-negative bacteria represent a challenging task for antibacterial drug discovery owing to their impermeable cell membrane and restricted uptake of small molecules. We herein describe the synthesis of natural-product-derived epoxycyclohexenones and explore their antibiotic activity against several pathogenic bacteria. A compound with activity against Salmonella Typhimurium was identified, and the target enzymes were unraveled by quantitative chemical proteomics. Importantly, two protein hits were linked to bacterial stress response, and corresponding assays revealed an elevated susceptibility to reactive oxygen species upon compound treatment. The consolidated inhibition of these targets provides a rationale for antibacterial activity and highlights epoxycyclohexenones as natural product scaffolds with suitable properties for killing Gram-negative Salmonella.
Intramolecular dipolar cycloaddition reaction of 5H,7H-thiazolo[3,4-c]oxazol-4-ium-l-olates: Synthesis of chiral 1H-pyrrolo[1,2-c]thiazole derivatives
Pinho Melo, Teresa M. V.,Barbosa, Dalia M.,Ramos, Paulo J. R. S.,Rocha Gonsalves, Antonio M.,Gilchrist, Thomas L.,Beja, Ana M.,Paixaeo, Jose A.,Silva, Manuela R.,Veiga, Luiz Alte Da
, p. 1219 - 1223 (2007/10/03)
(2R,4Ae)-Ar-AcyI-2-phenylthiazolidine-4-carboxylic acids were used to generate 5//,7//-thiazolo[3,4-c]oxazol-4-ium1-olates with internal dipolarophiles. The intramolecular 1,3-dipolar cycloaddition of these mesoionic species led to the synthesis of new l/
Generation and Cyclization of Acyl Radicals from Thiol Esters under Nonreducing, Tin-Free Conditions
Crich, David,Hao, Xiaolin
, p. 5982 - 5987 (2007/10/03)
The preparation of 2-(2-((tert-butyloxycarbonyl)amino)phenyl)ethyl mercaptan from 2-(2-aminophenyl)ethanol is described. This thiol is condensed with a series of suitably unsaturated carboxylic acids to give a series of thiol esters. The Boc group is remo
Photoinduced free radical chemistry of the acyl tellurides: Generation, inter- and intramolecular trapping, and ESR spectroscopic identification of acyl radicals
Crich, David,Chen, Chen,Hwang, Jae-Taeg,Yuan, Hongwei,Papadatos, Aristotle,Walter, Robert I.
, p. 8937 - 8951 (2007/10/02)
Acyl tellurides are prepared in good to excellent yield by the reaction of sodium aryl tellurides with acyl chlorides, or mixed anhydrides, and are found to be moderately air-stable substances. In contrast to previous literature reports, acyl tellurides of aryl and vinyl carboxylic acids are found to be excellent sources of acyl radicals on photolysis with a simple white light source. The acyl radicals so generated may be trapped intermolecularly by dichalcogenides, or by TEMPO in excellent yield. Trapping by N-tert-butyl-α-phenyl nitrone produces a stable nitroxide radical which has been characterized by ESR spectroscopy. The very efficient trapping of acyl radicals by acyl tellurides themselves is demonstrated by a crossover experiment. Acyl tellurides are shown to participate in very efficient radical cyclization reactions onto alkenes with the formation of five-, six-, and eight-membered rings. The immediate products of the cyclizations onto alkenes are α-[(aryltelluro)methyl] ketones and the chemistry of these relatively unstable species is briefly described. Treatment with hydrogen peroxide affords α-methylene ketones in high yield. When elimination of the aryl telluro group is not possible the α-[(aryltelluro)methyl] ketones are stable species that may subsequently be employed in further radical chain reactions, for example with tributyltin hydride and methyl acrylate. Cyclization onto alkynes yields α-[(aryltelluro)methylene] ketones which are stable species and which take part in substitution reactions with higher order cuprates or with diphenyl diselenide.
