(3R,4R,5S,6R)-2-(4-chloro-3-((5-(4-chlorobenzyl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | 1225430-55-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R,5S,6R)-2-(4-chloro-3-((5-(4-chlorobenzyl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: (3R,4R,5S,6R)-2-(4-Chloro-3-((5-(4-chlorobenzyl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol；(3R,4R,5S,6R)-2-[4-chloro-3-[[5-[(4-chlorophenyl)methyl]-1,3,4-thiadiazol-2-yl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1225430-55-6
• 化学式: C₂₂H₂₂Cl₂N₂O₅S
• 分子量: 497.399
• InChiKey: OTUSTAIHTBKJBP-SQGFOMTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 碘代三甲硅烷 作用下， 以 乙腈 为溶剂， 生成 (3R,4R,5S,6R)-2-(4-chloro-3-((5-(4-chlorobenzyl)-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