2-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetic acid | 1610956-00-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetic acid
• 英文别名: US9688710, 34 2-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetic acid；2-[4-[[2-methyl-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]phenyl]methyl]phenoxy]acetic acid
• CAS: 1610956-00-7
• 化学式: C₂₂H₂₆O₇S
• 分子量: 434.51
• InChiKey: XDOCGVQETVPCDZ-LXHROKJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-甲基丙氨酰胺 、 2-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetic acid 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 乙腈 为溶剂， 生成 2-methyl-2-(2-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetamido)propanamide
  参考文献：
  名称：

  Discovery of LX2761, a Sodium-Dependent Glucose Cotransporter 1 (SGLT1) Inhibitor Restricted to the Intestinal Lumen, for the Treatment of Diabetes

  摘要：

  The increasing number of people afflicted with diabetes throughout the world is a major health issue. Inhibitors of the sodium dependent glucose cotransporters (SGLT) have appeared as viable therapeutics to control blood glucose levels in diabetic patents. Herein we report the discovery of LX2761, a locally acting SGLT1 inhibitor that is highly potent in vitro and delays intestinal glucose absorption in vivo to improve glycemic control.

  DOI：

  10.1021/acs.jmedchem.6b01541
• 作为产物：
  描述：

  (2S,3S,4R,5S,6R)-2-(3-(4-hydroxybenzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 四丁基碘化铵 、 potassium carbonate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 2-(4-(2-methyl-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetic acid
  参考文献：
  名称：

  Discovery of LX2761, a Sodium-Dependent Glucose Cotransporter 1 (SGLT1) Inhibitor Restricted to the Intestinal Lumen, for the Treatment of Diabetes

  摘要：

  The increasing number of people afflicted with diabetes throughout the world is a major health issue. Inhibitors of the sodium dependent glucose cotransporters (SGLT) have appeared as viable therapeutics to control blood glucose levels in diabetic patents. Herein we report the discovery of LX2761, a locally acting SGLT1 inhibitor that is highly potent in vitro and delays intestinal glucose absorption in vivo to improve glycemic control.

  DOI：

  10.1021/acs.jmedchem.6b01541

文献信息

• INHIBITORS OF SODIUM GLUCOSE COTRANSPORTER 1
  申请人：Lexicon Pharmaceuticals, Inc.

  公开号：EP2925735B1

  公开（公告）日：2019-03-13
• Discovery of LX2761, a Sodium-Dependent Glucose Cotransporter 1 (SGLT1) Inhibitor Restricted to the Intestinal Lumen, for the Treatment of Diabetes
  作者：Nicole C. Goodwin、Zhi-Ming Ding、Bryce A. Harrison、Eric D. Strobel、Angela L. Harris、Melinda Smith、Andrea Y. Thompson、Wendy Xiong、Faika Mseeh、Debra J. Bruce、Damaris Diaz、Suma Gopinathan、Ling Li、Emily O’Neill、Mary Thiel、Alan G. E. Wilson、Kenneth G. Carson、David R. Powell、David B. Rawlins

  DOI：10.1021/acs.jmedchem.6b01541

  日期：2017.1.26

  The increasing number of people afflicted with diabetes throughout the world is a major health issue. Inhibitors of the sodium dependent glucose cotransporters (SGLT) have appeared as viable therapeutics to control blood glucose levels in diabetic patents. Herein we report the discovery of LX2761, a locally acting SGLT1 inhibitor that is highly potent in vitro and delays intestinal glucose absorption in vivo to improve glycemic control.