557087-95-3Relevant academic research and scientific papers
Synthesis of C-Analogues of β-Glucogallin and Aldose Reductase Inhibition Studies
Reddy, Mannem Rajeswara,Aidhen, Indrapal Singh,Shruthi, Karnam,Reddy, Geereddy Bhanuprakash
, p. 7283 - 7294 (2018/01/02)
β-Glucogallin 1 (BGG), a major component isolated from the Indian gooseberry (Emblica officinalis) medicinal plant, is a potent and selective inhibitor of aldose reductase (AKR1B1). Structurally, BGG is a glucosyl-1-ester, wherein gallic acid is linked to
Hantzsch-type three-component approach to a new family of carbon-linked glycosyl amino acids. Synthesis of C-glycosylmethyl pyridylalanines
Dondoni, Alessandro,Massi, Alessandro,Aldhoun, Mohammad
, p. 7677 - 7687 (2008/02/13)
(Chemical Equation Presented) C-Glycosylmethyl pyridylalanines reported in this paper constitute a novel family of glycosyl amino acids that contain a pyridine ring linking the carbohydrate and amino acid residues. These amino acids may serve to prepare n
Synthesis and in vitro biological evaluation of a carbon glycoside analogue of morphine-6-glucuronide
MacDougall, James M.,Zhang, Xiao-Dong,Polgar, Willma E.,Khroyan, Taline V.,Toll, Lawrence,Cashman, John R.
, p. 1583 - 1586 (2007/10/03)
Attachment of a glucose moiety to 6-β-aminomorphine afforded compound 3, where the glucose moiety was linked to the C-6 nitrogen atom by a two-carbon bridge. The synthesis of 3 was accomplished in eight steps from 3-triisopropylsilyl-6-β-aminomorphine and 2,3,4,6-tetra-O-benzyl-d-glucose. The C-glycoside 3 was prepared with the objective of examining a metabolically stable analogue of morphine-6-glucuronide and determining the potency and selectivity of opioid receptor binding. Competition binding assays showed that 3 bound to the μ opioid receptor with a Ki value of 3.5 nM. The C-glycoside 3 exhibited δ/μ and κ/μ selectivity ratios of 76 and 165, respectively. The synthetic intermediate (i.e., benzyl precursor, compound 11) bound to the μ opioid receptor with a Ki value of 0.5 nM, was less selective for the μ opioid receptor. The [35S] GTPγS assay was used to evaluate the functional properties of compounds 3 and 11. Compound 3 was determined to be a full agonist at the μ opioid receptor, whereas compound 11 was found to be a partial agonist. Compound 3 was determined to be very stable in the presence of human liver S9, and rat and monkey liver microsomes: no detectable loss of 3 was observed up to 90 min. Compound 3 was also very stable at pH 2 and pH 7.4, suggesting that 3 possessed properties for sustained duration of action.
Synthesis and partial biological evaluation of a small library of differentially-linked β-C-disaccharides
Postema, Maarten H. D.,Piper, Jared L.,Jie Shen, Lei Liu,Faust, Marcus,Andreana, Peter
, p. 4748 - 4754 (2007/10/03)
The synthesis of a small library of differentially-linked β-C-disaccharides has been carried out through the use of a radical allylation-RCM strategy. Acids 6 were prepared by Keck allylation of a suitable carbohydrate-based radical precursor, followed by
