58305-26-3Relevant academic research and scientific papers
'AND'-based fluorescence scaffold for the detection of ROS/RNS and a second analyte
Odyniec, Maria L.,Sedgwick, Adam C.,Swan, Alexander H.,Weber, Maria,Tang, T. M. Simon,Gardiner, Jordan E.,Zhang, Miao,Jiang, Yun-Bao,Kociok-Kohn, Gabriele,Elmes, Robert B. P.,Bull, Steven D.,He, Xiao-Peng,James, Tony D.
, p. 8466 - 8469 (2018/08/04)
Traditionally, fluorescence probes have focused on the detection of a single biomarker for a specific process. In this work, we set out to develop a number of fluorescence probes that enable the detection of a chosen analyte in the presence of reactive oxygen/nitrogen species (ROS/RNS). These fluorescence probes when activated result in the formation of the highly fluorescent pink dye, resorufin. Therefore, we have labelled these fluorescent probes as -Pinkments'. Our first -Pinkment' was shown to detect biologically relevant concentrations of ONOO- and have an excellent selectivity against other ROS/RNS. Pinkment-OH was developed to provide a core unit which could be easily functionalised to produce a range of -AND' based fluorescence probes for the detection of ROS/RNS and a second analyte. For proof of concept, we synthesised Pinkment-OTBS and Pinkment-OAc. These -AND'-based probes were successfully shown to detect ROS/RNS and F- or esterase, respectively.
Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation
Andrus, Merritt B.,Hicken, Erik J.,Stephens, Jeffrey C.,Bedke, D. Karl
, p. 8651 - 8654 (2007/10/03)
The total synthesis of the farnesyltransferase inhibitor kurasoin A has been achieved using a novel asymmetric phase-transfer-catalyzed glycolate alkylation reaction. 2,5-Dimethoxyacetophenone 7 with cinchonidinium catalyst 9 (10 mol %) and hydroxide base
Asymmetric phase-transfer catalyzed glycolate alkylation, investigation of the scope, and application to the synthesis of (-)-ragaglitazar
Andrus, Merritt B.,Hicken, Erik J.,Stephens, Jeffrey C.,Karl Bedke
, p. 9470 - 9479 (2007/10/03)
Asymmetric glycolate alkylation using a protected acetophenone surrogate under solid-liquid phase-transfer conditions is a new approach to the synthesis of 2-hydroxy esters and acids. Diphenylmethyloxy-2,5-dimethoxyacetophenone 1 with a trifluorobenzyl ci
Structure-activity relationships of the estrogenic sesquiterpene ester ferutinin. Modification of the terpenoid core
Appendino, Giovanni,Spagliardi, Paola,Sterner, Olov,Milligan, Stuart
, p. 1557 - 1564 (2007/10/03)
Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the α-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity.
