(2S,3R,4R,5S,6S)-2-acetoxymethyl-6-(4-chloro-3-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 1259018-25-1

• 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,6S)-2-acetoxymethyl-6-(4-chloro-3-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• 英文别名: [(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[4-chloro-3-[[5-(furan-2-yl)-1,3,4-thiadiazol-2-yl]methyl]phenyl]oxan-2-yl]methyl acetate
• CAS: 1259018-25-1
• 化学式: C₂₇H₂₇ClN₂O₁₀S
• 分子量: 607.038
• InChiKey: XGPOMDDUWZXSHI-PKSHOOMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  182
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S,6S)-2-acetoxymethyl-6-(4-chloro-3-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 甲醇 、 sodium methylate 作用下， 反应 2.0h， 以78 mg的产率得到(2S,3R,4R,5S,6R)-2-(4-chloro-3-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: 1,3,4-Thiadiazolylmethylphenyl glucoside congeners

  摘要：

  Novel C-aryl glucoside SGLT2 inhibitors containing 1,3,4-thiadiazole moieties were designed and synthesized. Among the compounds tested, biaryl-type compounds containing pyrazine 59, 2-furan 61, and 3-thiophene 71 showed the best in vitro inhibitory activities to date (IC50 = 3.51-7.03 nM) against SGLT2. A selected compound 61, demonstrated reasonable blood glucose-lowering effects, indicating that the information obtained from the SAR studies in this 1,3,4-thiadiazolylmethylphenyl glucoside series might help to design more active SGLT2 inhibitors that are structurally related. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.073
• 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)benzyl)-5-(furan-2-yl)-1,3,4-thiadiazole 、 乙酸酐 在 碘代三甲硅烷 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙腈 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S,3R,4R,5S,6S)-2-acetoxymethyl-6-(4-chloro-3-((5-(furan-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: 1,3,4-Thiadiazolylmethylphenyl glucoside congeners

  摘要：

  Novel C-aryl glucoside SGLT2 inhibitors containing 1,3,4-thiadiazole moieties were designed and synthesized. Among the compounds tested, biaryl-type compounds containing pyrazine 59, 2-furan 61, and 3-thiophene 71 showed the best in vitro inhibitory activities to date (IC50 = 3.51-7.03 nM) against SGLT2. A selected compound 61, demonstrated reasonable blood glucose-lowering effects, indicating that the information obtained from the SAR studies in this 1,3,4-thiadiazolylmethylphenyl glucoside series might help to design more active SGLT2 inhibitors that are structurally related. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.073

文献信息

• [EN] NOVEL C-ARYL GLUCOSIDE SGLT2 INHIBITORS AND PHARMACEUTICAL COMPOSITION COMPRISING SAME<br/>[FR] NOUVEAUX INHIBITEURS DE SGLT2 CONSISTANT EN C-ARYL GLUCOSIDES ET COMPOSITION PHARMACEUTIQUE LES COMPRENANT
  申请人：GREEN CROSS CORP

  公开号：WO2010147430A3

  公开（公告）日：2011-05-05