79250-47-8Relevant academic research and scientific papers
A Structure-Reactivity Relationship of the Tandem Asymmetric Dihydroxylation on a Biologically Relevant Diene: Influence of Remote Stereocenters on Diastereofacial Selectivity
Gill, Daniel M.,Male, Louise,Jones, Alan M.
, p. 7568 - 7577 (2019)
The Sharpless asymmetric dihydroxylation (AD) finds widespread use in natural product and drug molecule syntheses, in part, due to its efficiency and predictability. However, the tandem AD of dienes is much less studied, but important in complex molecular synthesis. Herein, a biologically relevant tandem AD is reported, and several anomalies are discovered with the accepted model. These include the formation of unpredicted diastereoisomers, with matched and mismatched stereocenters contradicting the Sharpless mnemonic device. From a structural analysis of the tandem AD, we present a strategy to improve asymmetric induction in sterically hindered alkenes using double diastereodifferentiation from a 9-bond distant stereocenter. A theoretical justification for the unpredicted stereoselectivity, accounting for the influence of steric hindrance and pre-installed chirality, is proposed.
GLYCOMIMETICS FOR USE FOR THE TREATMENT OF VASCULAR CALCIFICATION AND/OR ENDOTHELIAL DYSFUNCTION
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Page/Page column 62, (2017/03/28)
The present invention relates to the use of glycomimetic compounds for the treatment of vascular calcification and/or endothelial dysfunction, particularly the use of small molecule mimetics of heparin/heparan sulfate, such as compounds according to formula (A), (B), (C) or (D), or pharmaceutically acceptable derivatives thereof
Novel heparin/heparan sulfate mimics as inhibitors of HGF/SF-induced MET activation
Raiber, Eun-Ang,Wilkinson, James A.,Manetti, Fabrizio,Botta, Maurizio,Deakin, Jon,Gallagher, John,Lyon, Malcolm,Ducki, Sylvie W.
, p. 6321 - 6325 (2008/09/17)
The synthesis of simple, non-sugar glycosaminoglycan (GAG) mimics has been achieved and the analogues evaluated for their ability to inhibit the activation of the MET receptor by hepatocyte growth factor/scatter factor (HGF/SF).
Substituted phenoxyacetic acids
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, (2008/06/13)
Disclosed are substituted phenoxyacetic acids useful in the treatment of chronic complications arising from diabetes mellitus. Also disclosed are pharmaceutical compositions containing the compounds, alone or in combination with other therapeutic agents, and methods of treatment employing the compounds and pharmaceutical compositions, as well as methods for their synthesis.
A biomimetic approach to dihydrobenzofuran synthesis
Benbow,Katoch-Rouse
, p. 4965 - 4972 (2007/10/03)
A method for an acid-catalyzed construction of dihydrobenzofuran heterocycles (14) from 2-(2′-hydroxyethyl)quinone precursors 10 is presented. The putative oxonium ion intermediate 17 formed by an intramolecular hydroxyl cyclization followed by dehydration is reduced in situ by an added dihydroquinone source. Good to excellent yields of cyclized products are realized in all cases except for highly electron deficient systems, and these suffer reduction prior to oxonium ion formation. All products are monomeric and derived from a two-electron transfer except for 10g, which affords the dimeric dihydrobenzofuran. The amount of cyclization or reduction product is governed by the HOMO/LUMO gap between the quinone substrate and the dihydroquinone additive, and the product distribution can be adjusted by modifying the electronic properties of the added reducing agent.
