73174-45-5Relevant academic research and scientific papers
Design, synthesis and biological evaluation of 6-deoxy O-spiroketal C-arylglucosides as novel renal sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes
Wang, Yibing,Lou, Yang,Wang, Jiang,Li, Dan,Chen, Hui,Zheng, Tiannan,Xia, Chunmei,Song, Xiaohan,Dong, Tiancheng,Li, Jingya,Li, Jia,Liu, Hong
, p. 398 - 416 (2019/07/19)
In this work, aiming at finding a novel, potent, and selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor with good pharmacokinetic profiles for the treatment of diabetes, we focus on modifying the sugar moiety of SGLT2 inhibitors, which dominates the binding with glucose binding site of hSGLT, via removing the C-6 hydroxy group to adjust the physicochemical properties and target-recognition manners of SGLT2 inhibitors. In addition, tofogliflozin containing a special O-spiroketal C-arylglucoside scaffold, displayed good efficacy and bioavailability both in animals and in humans. Therefore, a series of 6-deoxy O-spiroketal C-arylglucosides as novel SGLT2 inhibitors were designed, synthesized, and evaluated in this work. The structure-activity relationship (SAR) research on this novel series and a comprehensive in vitro and in vivo biological evaluation afforded compound 39 with high in vitro hSGLT2 inhibitory activity (IC50 = 4.5 nM), good pharmacokinetic profiles, and more remarkable efficacy in C57BL/6J mice and Sprague-Dawley rats than marketed drug tofogliflozin.
C,O-SPIRO ARYL GLYCOSIDE COMPOUNDS, PREPARATION THEREFOR AND USE THEREOF
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, (2018/05/16)
The present invention provides C, O-spiro aryl glycoside compounds, preparation therefor and use thereof. Specifically provided are the compounds represented by the formula (I), wherein the definitions of each group are described in the specification. The
Iodine monochloride (ICl) as a highly efficient, green oxidant for the oxidation of alcohols to corresponding carbonyl compounds
Wei, Peng,Zhang, Datong,Gao, Zhigang,Cai, Wenqing,Xu, Weiren,Tang, Lida,Zhao, Guilong
, p. 1457 - 1470 (2015/05/20)
Iodine monochloride (ICl) was discovered to be a highly efficient, green oxidant, which can oxidize aldose hemiacetals, diarylmethanols, arylalkylmethanols, anddialkylmethanols to the corresponding aldose lactones, diarylmethanones, arylalkylmethanones, and dialkylmethanones, respectively, in high yields. ICl as a green, metal-free oxidant is characterized by mild reaction condition, short reaction time, good yield, and broad scope.
PHENYL C-GLUCOSIDE DERIVATIVE CONTAINING DEOXYGLUCOSE STRUCTURE, PREPARATION METHOD AND USE THEREOF
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Paragraph 0249; 0250; 0251; 0252, (2015/11/09)
The present invention provides a phenyl C-glucoside derivative containing a deoxyglucose structure as represented by formula I, preparation method thereof, a pharmaceutical composition comprising the same, and uses thereof in the preparation of medicament
Mannose-binding geometry of pradimicin A
Nakagawa, Yu,Doi, Takashi,Taketani, Takara,Takegoshi,Igarashi, Yasuhiro,Ito, Yukishige
, p. 10516 - 10525 (2013/08/23)
Pradimicins (PRMs) and benanomicins are the only family of non-peptidic natural products with lectin-like properties, that is, they recognize D-mannopyranoside (Man) in the presence of Ca2+ ions. Coupled with their unique Man binding ability, t
A facile synthesis of 6-deoxydapagliflozin
Shi, Yongheng,Xu, Huaqiang,Liu, Bingni,Kong, Weiling,Wei, Qunchao,Xu, Weiren,Tang, Lida,Zhao, Guilong
, p. 1903 - 1910 (2014/01/06)
A facile synthesis of a potent SGLT2 inhibitor, 6-deoxydapagliflozin, from methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-d-glucopyranoside in six steps with an overall yield of 50 % is described. The key steps were the reductive deiodination of the starting
β-Rhamnosides from 6-thio mannosides
Christina, Alphert E.,Es, Daan Van Der,Dinkelaar, Jasper,Overkleeft, Hermen S.,Marel, Gijsbert A. Van Der,Codee, Jeroen D. C.
supporting information; experimental part, p. 2686 - 2688 (2012/04/10)
Upon condensation of 6-thio-6-deoxy-mannosyl donors 1,2-cis products are obtained with a high degree of stereoselectivity. Subsequent reductive removal of the 6-thio functionality gives 1,2-cis rhamnosides. The 1,2-cis-selectivity can be rationalized with
Zinc-mediated fragmentation of methyl 6-deoxy-6-iodo-hexopyranosides
Skaanderup, Philip R.,Hyldtoft, Lene,Madsen, Robert
, p. 467 - 472 (2007/10/03)
An improved procedure was developed for the zinc-mediated fragmentation of protected and unprotected methyl 6-deoxy-6-iodo-hexopyranosides. The method employs sonication of the iodoglycoside with zinc dust in a THF/H2O mixture.
The use of a new magnesium-derived hydride reagent for carbohydrate derivatives
Szabovik,Medgyes,Antal,Varga,Knott,Liptak
, p. 1003 - 1009 (2007/10/03)
The magnesium hydride based reagent in THF solution is an excellent tool for the stereoselective reduction of different uloside derivatives. Sugar azides, sulfonyl esters give aminosugars and methylose derivatives without affecting other functionalities. Halogenated sugars or methylene derivatives are stable under these conditions. The reagent can be applied in the presence of a wide variety of blocking groups (acetals, benzyl and allyl ethers, imides, C=C bonds) generally used in the carbohydrate chemistry.
