27108-07-2Relevant academic research and scientific papers
5-FLUORO-C-(ARYL OR HETEROCYCLYL)-GLYCOSIDE DERIVATIVES USEFUL AS DUAL SGLT1 / SGLT2 MODULATORS
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Paragraph 0415, (2019/02/28)
The present invention is directed to 5-fluoro-C-(aryl or hetercyclyl)-glycoside derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT activity, more particularly dual SGLT1/2 activity.
NOVEL FLUOROGLYCOSIDE HETEROCYCLIC DERIVATIVES, PHARMACEUTICAL PRODUCTS CONTAINING SAID COMPOUNDS AND THE USE THEREOF
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Page/Page column 33-34, (2008/06/13)
The invention relates to substituted fluoroglycoside heterocyclic derivatives of a formula (I), wherein radicals have predefined bonds, to the psychologically tolerated salts thereof and to methods for the preparation thereof. Said compounds can be used, for example as antidiabetic agents.
Synthesis of UDP-4-deoxy-4-fluoroglucose and UDP-4-deoxy-4-fluorogalactose and their interactions with enzymes of nucleotide sugar metabolism
Chapeau,Frey
, p. 6994 - 6998 (2007/10/02)
Fluorinated carbohydrates can be used as probes of enzymatic active sites. We report the synthesis of 4-deoxy-4-fluoro-α-D-galactose-1-phosphate and the substrate analogues of UDP-galactose, UDP4-deoxy-4-fluoro-α-D-galactose (UDP-FGal), and of UDP-glucose, UDP-4-deoxy-4-fluoro-α-D-glucose (UDP-FGlc), which may be useful in analyzing the binding properties of enzymes that utilize nucleotide sugars as substrates. As a first step in this study, we determine the kinetic and inhibition parameters for UDP-FGal and UDP-FGlc interacting with UDP-glucose dehydrogenase and UDP-galactose 4-epimerase. UDP-FGlc is a substrate for bovine liver UDP-glucose dehydrogenase: K(m) = 30.2 ± 4.5 μM slightly higher than the value 9.6 ± 0.7 μM for UDP-glucose, and V(m)(UDP-FGlc) = 0.46V(mUDP-Glc). UDP-FGal is not a substrate for UDP-glucose dehydrogenase but is a competitive inhibitor with respect to UDP-glucose (K(i) = 19.9 ± 6.6 μM). These analogs also bind to UDP-galactose 4-epimerase from E. coli with dissociation constants K(d) of 1.4 and 1.1 mM for UDP-FGlc and UDP-FGal, respectively.
THE SYNTHESIS AND HYDROLYSIS OF A SERIES OF DEOXYFLUORO-D-GLUCOPYRANOSYL PHOSPHATES
Withers, Stephen G.,MacLennan, David J.,Street, Ian P.
, p. 127 - 144 (2007/10/02)
The synthesis of all four deoxyfluoro-α-D-glucopyranosyl phosphates is described.Rate conctants for their acid-catalyzed hydrolysis were determined, and fluorine substitution was shown to have a significant effect in lowering the rate, particularly when t
