(2S,3S,4R,5R,6S)-methyl 6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-3,4,5-trihydroxy-tetrahydro-2H-pyran-2-carboxylate | 1270018-45-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5R,6S)-methyl 6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-3,4,5-trihydroxy-tetrahydro-2H-pyran-2-carboxylate
• 英文别名: (2S,3S,4R,5R,6S)-methyl 6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate；methyl (2S,3S,4R,5R,6S)-6-[4-chloro-3-[[5-(furan-2-yl)-1,3-thiazol-2-yl]methyl]phenyl]-3,4,5-trihydroxyoxane-2-carboxylate
• CAS: 1270018-45-5
• 化学式: C₂₁H₂₀ClNO₇S
• 分子量: 465.911
• InChiKey: AYBPPTQVTACQNX-SLHNCBLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)acetic acid 在 劳森试剂 、 N-甲基吗啉 、 sodium chlorite 、 potassium dihydrogenphosphate 、 三氟甲磺酸三甲基硅酯 、 乙酸酐 、 三氯化硼 、 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 2-甲基-2-丁烯 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 35.0h， 生成 (2S,3S,4R,5R,6S)-methyl 6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-3,4,5-trihydroxy-tetrahydro-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Exploration of SAR regarding glucose moiety in novel C-aryl glucoside inhibitors of SGLT2

  摘要：

  In order to investigate SAR regarding glucose moiety in novel C-aryl glucoside SGLT2 inhibitors containing a thiazole motif, a series of chemical modifications on glucose was conducted to explore potential utility as a suitable replacement of glucose per se. Among the compounds prepared, deshydroxy 29 (IC50 = 7.01 nM) demonstrated the best in vitro inhibitory activity against SGLT2 in this series to date. But, none of the compounds were better than the parent molecule 5 (IC50 = 1.75 nM). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.115

文献信息

• Exploration of SAR regarding glucose moiety in novel C-aryl glucoside inhibitors of SGLT2
  作者：Eun-Jung Park、Younggyu Kong、Jun Sung Lee、Sung-Han Lee、Jinhwa Lee

  DOI：10.1016/j.bmcl.2010.11.115

  日期：2011.1

  In order to investigate SAR regarding glucose moiety in novel C-aryl glucoside SGLT2 inhibitors containing a thiazole motif, a series of chemical modifications on glucose was conducted to explore potential utility as a suitable replacement of glucose per se. Among the compounds prepared, deshydroxy 29 (IC50 = 7.01 nM) demonstrated the best in vitro inhibitory activity against SGLT2 in this series to date. But, none of the compounds were better than the parent molecule 5 (IC50 = 1.75 nM). (C) 2010 Elsevier Ltd. All rights reserved.