132201-75-3Relevant academic research and scientific papers
Decarboxylative glycosylation reaction - Intra- versus intermolecular reaction course
Scheffler, Goetz,Schmidt, Richard R.
, p. 2943 - 2946 (1997)
Mixed glycosyl carbonates are transformed under acid catalysis into glycosides. Competition experiments with equal amounts of carbonates 5 and 6 led to complete scrambling of the glycosyl donor and acceptor moieties: not only the expected glycosides 7 and
Synthesis and NMR binding study of a chiral spirocyclic helical analogue of a natural DNA bulge binder
Gaikwad, Nilesh W.,Hwang, Geum-Sook,Goldberg, Irving H.
, p. 4833 - 4836 (2004)
(Chemical Equation Presented) Synthesis of chiral spirocyclic helical compounds which mimic the molecular architecture of the potent DNA bulge binder obtained from the antitumor agent NCS-chrom has been accomplished. Structural analysis of the compounds b
Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**
Holmstr?m, Thomas,Nielsen, Michael Martin,Pedersen, Christian Marcus
supporting information, (2021/12/30)
Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective
Synthesis of nature product kinsenoside analogues with anti-inflammatory activity
Song, Wei,Sun, Yong,Xu, Lintao,Sun, Yajing,Li, Tianlu,Peng, Peng,Lou, Hongxiang
supporting information, (2020/12/02)
Kinsenoside is the major bioactive component from herbal medicine with a broad range of pharmacological functions. Goodyeroside A, an epimer of kinsenoside, remains less explored. In this report we chemically synthesized kinsenoside, goodyeroside A and their analogues with glycan variation, chirality inversion at chiral center(s), and bioisosteric replacement of lactone with lactam. Among these compounds, goodyeroside A and its mannosyl counterpart demonstrated superior anti-inflammatory efficacy. Furthermore, goodyeroside A was found to suppresses inflammatory through inhibiting NF-κB signal pathway, effectively. Structure-activity relationship is also explored for further development of more promising kinsenoside analogues as drug candidates.
Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof
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Paragraph 0033; 0057; 0063, (2021/04/03)
The invention discloses a beta-D-glucose short-chain fatty acid ester compound as well as a preparation method and application thereof, and belongs to the technical field of organic synthesis. The compound is a compound shown as a formula I, or a stereoisomer, a pharmaceutically acceptable salt, a solvate or a prodrug of the compound shown as the formula I. The formula is as shown in the description, wherein R is a methyl group, an ethyl group, a propyl group, a propylene group, an isopropylidene group, a butyl group, a butylidene group, an isobutylidene group, an amyl group, a pentylidene group or an isoamylidene group. The compound has potential prevention and treatment effects on diabetes, hyperlipidemia, atherosclerosis, Alzheimer's disease, cardiovascular and cerebrovascular diseases,inflammation, tumors and depression.
Substituted pyrazole compound, preparation method, pharmaceutical composition and applications thereof
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Paragraph 270; 0287-0290, (2020/03/12)
The invention discloses a substituted pyrazole compound represented by a formula I, and a preparation method, a pharmaceutical composition and applications thereof, wherein the compound has characteristics of good stability, excellent solubility, low cytotoxicity and remarkable neuroprotective effect, can effectively prevent and treat nerve cell injury, and is an ideal medicinal compound for preventing or treating cerebral stroke, cerebral embolism, cerebral stroke sequelae, cerebral stroke dyskinesia, mitochondrial encephalomyopathy and amyotrophic lateral sclerosis of spinal cord.
Visible-Light-Mediated β-C(sp3)-H Amination of Glycosylimidates: En Route to Oxazoline-Fused/Spiro Nonclassical Bicyclic Sugars
Shaw, Mukta,Kumar, Amit
supporting information, (2019/05/08)
A straightforward route has been developed for the diastereoselective synthesis of nonclassical conformationally constrained oxazoline-fused and spiro bicyclic sugars bearing a quaternary center via selective β-C-H amination of appropriately positioned gl
An Empirical Understanding of the Glycosylation Reaction
Chatterjee, Sourav,Moon, Sooyeon,Hentschel, Felix,Gilmore, Kerry,Seeberger, Peter H.
supporting information, p. 11942 - 11953 (2018/09/27)
Reliable glycosylation reactions that allow for the stereo- and regioselective installation of glycosidic linkages are paramount to the chemical synthesis of glycan chains. The stereoselectivity of glycosylations is exceedingly difficult to control due to the reaction's high degree of sensitivity and its shifting, simultaneous mechanistic pathways that are controlled by variables of unknown degree of influence, dominance, or interdependency. An automated platform was devised to quickly, reproducibly, and systematically screen glycosylations and thereby address this fundamental problem. Thirteen variables were investigated in as isolated a manner as possible, to identify and quantify inherent preferences of electrophilic glycosylating agents (glycosyl donors) and nucleophiles (glycosyl acceptors). Ways to enhance, suppress, or even override these preferences using judicious environmental conditions were discovered. Glycosylations involving two specific partners can be tuned to produce either 11:1 selectivity of one stereoisomer or 9:1 of the other by merely changing the reaction conditions.
Fluorine-Directed Glycosylation Enables the Stereocontrolled Synthesis of Selective SGLT2 Inhibitors for Type II Diabetes
Sadurní, Anna,Kehr, Gerald,Ahlqvist, Marie,Wernevik, Johan,Sj?gren, Helena Peilot,Kankkonen, Cecilia,Knerr, Laurent,Gilmour, Ryan
, p. 2832 - 2836 (2017/12/26)
Inhibition of the sodium-glucose co-transporters (SGLT1 and SGLT2) is a validated strategy to address the increasing prevalence of type II diabetes mellitus. However, achieving selective inhibition of human SGLT1 or SGLT2 remains challenging. Orally available small molecule drugs based on the d-glucose core of the natural product Gliflozin have proven to be clinically effective in this regard, effectively impeding glucose reabsorption. Herein, we disclose the influence of molecular editing with fluorine at the C2 position of the pyranose ring of Phlorizin analogues Remogliflozin Etabonate and Dapagliflozin (Farxiga) to concurrently direct β-selective glycosylation, as is required for biological efficacy, and enhance aspects of the physicochemical profile. Given the abundance of glycosylated pharmaceuticals in diabetes therapy that contain a β-configured d-glucose nucleus, it is envisaged that this strategy may prove to be expansive.
REAGENTS AND METHODS FOR GLYCOSYLATION
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Paragraph 00173, (2018/03/09)
The invention provides methods and regents for the glycosylation of organic molecules. In one aspect, the invention provides a method for glycosylating a hydroxyl-containing organic compound (i.e., a glycosyl acceptor) comprising contacting a glycosyl don
