(2S,3R,4R,5S,6R)-2-(3-(4-ethylbenzyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | 333360-64-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5S,6R)-2-(3-(4-ethylbenzyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: (2S,3R,4R,5S,6R)-2-[3-[(4-ethylphenyl)methyl]-4-methylphenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 333360-64-8
• 化学式: C₂₂H₂₈O₅
• 分子量: 372.461
• InChiKey: IOUMMDDMHYSAMP-BDHVOXNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S,6R)-2-(3-(4-ethylbenzyl)-4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 、 苯甲醛二甲缩醛 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Syntheses of C-5-spirocyclic C-glycoside SGLT2 inhibitors

  摘要：

  Several syntheses of C-5-spirocycle-containing C-glycosides are discussed. A multigram-scale synthesis capitalizing on a one-pot aldol-Cannizzaro sequence is described. Spiro oxetane formation using an unprotected penta-ol C-glycoside as substrate is also exemplified. Functional assessment of these compounds for potency and selectivity was evaluated at human SGLT2 and SGLT1. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.024

文献信息

• C-Aryl glycoside inhibitors of SGLT2: Exploration of sugar modifications including C-5 spirocyclization
  作者：Ralph P. Robinson、Vincent Mascitti、Carine M. Boustany-Kari、Christopher L. Carr、Patrick M. Foley、Emi Kimoto、Michael T. Leininger、Andre Lowe、Michelle K. Klenotic、James I. MacDonald、Robert J. Maguire、Victoria M. Masterson、Tristan S. Maurer、Zhuang Miao、Jigna D. Patel、Cathy Préville、Matthew R. Reese、Li She、Claire M. Steppan、Benjamin A. Thuma、Tong Zhu

  DOI：10.1016/j.bmcl.2010.01.075

  日期：2010.3

  Modifications to the sugar portion of C-aryl glycoside sodium glucose transporter 2 (SGLT2) inhibitors were explored, including systematic deletion and modification of each of the glycoside hydroxyl groups. Based on results showing activity to be quite tolerant of structural change at the C-5 position, a series of novel C-5 spiro analogues was prepared. Some of these analogues exhibit low nanomolar potency versus SGLT2 and promote urinary glucose excretion (UGE) in rats. However, due to sub-optimal pharmacokinetic parameters (in particular half-life), predicted human doses did not meet criteria for further advancement. (C) 2010 Elsevier Ltd. All rights reserved.
• GLUCOPYRANOSYL-SUBSTITUTED BENZENE DERIVATIVES, MEDICAMENTS CONTAINING SUCH COMPOUNDS, THEIR USE AND PROCESS FOR THEIR MANUFACTURE
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP1828216B1

  公开（公告）日：2008-09-10
• METHODS FOR PREVENTING AND TREATING NEURODEGENERATIVE DISORDERS
  申请人：Wienrich Marion

  公开号：US20100081625A1

  公开（公告）日：2010-04-01

  The present invention relates to a method for treating, preventing or slowing, delaying or reversing progression of one or more neurodegenerative disorders in a patient in need thereof characterized by administering a glucopyranosyl-substituted benzene derivative, a tautomer, stereoisomer, mixture or salt thereof, as defined in claim 1 to the patient in need thereof.
• US7687469B2
  申请人：——

  公开号：US7687469B2

  公开（公告）日：2010-03-30