| 1221496-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1221496-25-8
• 化学式: C₄₃H₄₆O₅
• 分子量: 642.835
• InChiKey: GSLNHOSENOUAQX-FLOOJLJVSA-N

反应信息

• 作为反应物：
  描述：

  在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 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
• 作为产物：
  描述：

  在 aluminum (III) chloride 、 lithium aluminium tetrahydride 作用下， 以 乙醚 、 二氯甲烷 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.