26215-90-7Relevant articles and documents
Small molecule probes of the receptor binding site in the Vibrio cholerae CAI-1 quorum sensing circuit
Bolitho, Megan E.,Perez, Lark J.,Koch, Matthew J.,Ng, Wai-Leung,Bassler, Bonnie L.,Semmelhack, Martin F.
experimental part, p. 6906 - 6918 (2012/01/03)
Based on modification of separate structural features of the Vibrio cholerae quorum sensing signal, (S)-3-hydroxytridecan-4-one (CAI-1), three focused compound libraries have been synthesized and evaluated for biological activity. Modifications to the acyl tail and α-hydroxy ketone typically provided agonists with activities correlated to tail length and conservative changes to the hydroxy ketone. Among the molecules identified within this collection of agonists is Am-CAI-1 (B11), which is among the most potent agonists reported to date with an EC50 of 0.21 μM. Modifications to the ethyl side chain delivered molecules with both agonist and antagonist activity, including m-OH-Ph-CAI-1 (C13) which is the most potent antagonist reported to date with an IC50 of 36 μM. The molecules described in this manuscript are anticipated to serve as valuable tools in the study of quorum sensing in Vibrio cholerae and provide new leads in the development of an antivirulence therapy against this human pathogen.
Catalytic ketonisation over oxide catalysts. Part IX. Single step synthesis of aliphatic saturated and unsaturated C11 - C 13 ketones from carboxylic acids
Glinski,Gibka
, p. 299 - 302 (2007/10/03)
Metameric undecan-x-ones (x = 2-6), dodecan-y-ones (y = 2-5), tridecan-z-ones (z = 4-7) and two unsaturated aliphatic ketones were prepared by vapor phase ketonisation of the appropriate monocarboxylic acids in the presence of 20 wt% MnO2/Al2O3 catalyst under flow conditions. The ketones were obtained in yields between 48 and 89% in a multigram scale (80-250 g). Their physical and spectral data have been determined.
Copper-catalysed aerobic oxidation of alcohols using fluorous biphasic catalysis
Ragagnin, Gianna,Betzemeier, Bodo,Quici, Silvio,Knochel, Paul
, p. 3985 - 3991 (2007/10/03)
A copper(I) catalysed and TEMPO mediated fluorous biphasic oxidation of primary, secondary, allylic and benzylic alcohols with oxygen in the presence of a bipyridine ligand bearing perfluorinated ponytails is described. High chemoselectivities are observed in the oxidation of substituted cyclohexanols (substituted axial cyclohexanols react 6-8 times faster than the corresponding equatorial cyclohexanols).