(2S,3R,4R,5S,6R)-2-(3-((5-(benzo[b]thiophen-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol | 1225430-90-9

• 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,6R)-2-(3-((5-(benzo[b]thiophen-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: (2S,3R,4R,5S,6R)-2-(4-chloro-3-((5-(benzo[b]thiophen-2-yl)-1,3,4-thiadiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2S,3R,4R,5S,6R)-2-(3-((5-(Benzo[b]thiophen-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol；(2S,3R,4R,5S,6R)-2-[3-[[5-(1-benzothiophen-2-yl)-1,3,4-thiadiazol-2-yl]methyl]-4-chlorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1225430-90-9
• 化学式: C₂₃H₂₁ClN₂O₅S₂
• 分子量: 505.015
• InChiKey: SYAMQOJQFQKMQT-JLMLEOCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  172
• 氢给体数：
  4
• 氢受体数：
  9

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 (2S,3R,4R,5S,6R)-2-(3-((5-(benzo[b]thiophen-2-yl)-1,3,4-thiadiazol-2-yl)methyl)-4-chlorophenyl)-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

文献信息

• NOVEL C-ARYL GLUCOSIDE SGLT2 INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAME
  申请人：Lee Jinhwa

  公开号：US20120101051A1

  公开（公告）日：2012-04-26

  A novel C-aryl glucoside compound, or a pharmaceutically acceptable salt or a prodrug thereof having an inhibitory activity against sodium-dependent glucose cotransporter 2 (SGLT2) being present in the intestine and kidney; and a pharmaceutical composition comprising the same as an active ingredient, which is useful for preventing or treating metabolic disorders, particularly, diabetes, are provided.

  提供了一种新型的C-芳基葡萄糖苷化合物，或其药学上可接受的盐或前药，具有抑制肠道和肾脏中存在的钠依赖性葡萄糖共转运体2（SGLT2）的活性；以及包含该化合物作为活性成分的制药组合物，可用于预防或治疗代谢性疾病，特别是糖尿病。
• US8541380B2
  申请人：——

  公开号：US8541380B2

  公开（公告）日：2013-09-24