(2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)methanol | 1225430-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)methanol
• 英文别名: (2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxy-methyl)-tetrahydro-2H-pyran-2-yl)phenyl)methanol；(2-Chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)methanol；[2-chloro-5-[(3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]phenyl]methanol
• CAS: 1225430-37-4
• 化学式: C₄₁H₄₁ClO₆
• 分子量: 665.226
• InChiKey: UADFTCYVPJNAQE-MKDQTQJASA-N

物化性质

• 沸点：
  770.1±60.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)methanol 在 劳森试剂 、 N-甲基吗啉 、 吡啶 、 2,6-二甲基吡啶 、 碘代三甲硅烷 、 水 、 三溴化磷 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 72.0h， 生成 butyl ((2R,3S,4R,5R,6S)-6-(4-chloro-3-((5-(thiophen-3-yl)thiazol-2-yl)methyl)phenyl)-3,4,5-trihydroxy-tetrahydro-2H-pyran-2-yl)methyl carbonate
  参考文献：
  名称：

  [EN] THIAZOLE DERIVATIVES AS SGLT2 INHIBITORS AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  [FR] DÉRIVÉS DE THIAZOLE EN TANT QU'INHIBITEURS DE SGLT2 ET COMPOSITION PHARMACEUTIQUE COMPRENANT CEUX-CI

  摘要：

  公开号：

  WO2011159067A3
• 作为产物：
  描述：

  (2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 (2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)methanol
  参考文献：
  名称：

  Novel C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents: Pyridazinylmethylphenyl glucoside congeners

  摘要：

  Novel C-aryl glucoside SGLT2 inhibitors containing pyridazine motif were designed and synthesized for biological evaluation. Among the compounds tested, pyridazine containing methylthio moiety 22l or thiadiazole ring 22ah showed the best in vitro inhibitory activities in this series (IC50 = 13.4, 11.4 nM, respectively) against SGLT2 to date. Subsequently, compound 22l exhibited reasonable urinary glucose excretion and glucosuria in normal SD rats, thereby demonstrating that this pyridazine series possesses both in vitro SGLT2 inhibition and in vivo efficacy, albeit to a lower degree. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.006

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。
• Thiazole derivatives as SGLT2 inhibitors and pharmaceutical composition comprising same
  申请人：Lee Jinhwa

  公开号：US08586550B2

  公开（公告）日：2013-11-19

  The present invention relates to a novel compound with thiazole ring 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.

  本发明涉及一种新型含噻唑环的化合物，具有对存在于肠和肾中的钠依赖性葡萄糖协同转运体2（SGLT2）的抑制活性，以及包含该化合物作为活性成分的药物组合物，可用于预防或治疗代谢性疾病，特别是糖尿病。
• Thiazole Derivatives as SGLT2 Inhibitors and Pharmaceutical Composition Comprising Same
  申请人：Lee Jinhwa

  公开号：US20130090298A1

  公开（公告）日：2013-04-11

  The present invention relates to a novel compound with thiazole ring 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.

  本发明涉及一种新型含有噻唑环的化合物，具有对存在于肠和肾中的钠依赖性葡萄糖共转运体2（SGLT2）的抑制活性，以及包含该化合物作为活性成分的制药组合物，用于预防或治疗代谢性疾病，特别是糖尿病。
• NOVEL DIPHENYLMETHANE DERIVATIVES AS SGLT2 INHIBITORS
  申请人：Choi Soongyu

  公开号：US20140088079A1

  公开（公告）日：2014-03-27

  The present invention relates to a compound with a diphenylmethane moiety 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. The present invention also provides a method for preparing the compound, and a method for preventing or treating metabolic disorders, particularly diabetes, by using the compound.

  本发明涉及一种具有二苯甲烷基团的化合物，其具有对存在于肠和肾中的钠依赖性葡萄糖共转运体2（SGLT2）的抑制活性，以及包含该化合物作为活性成分的制药组合物，用于预防或治疗代谢性疾病，尤其是糖尿病。本发明还提供了一种制备该化合物的方法，以及使用该化合物预防或治疗代谢性疾病，尤其是糖尿病的方法。
• C-aryl glucoside SGLT2 inhibitors and pharmaceutical compositions comprising same
  申请人：Lee Jinhwa

  公开号：US08541380B2

  公开（公告）日：2013-09-24

  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.

  提供一种新的C-芳基葡萄糖苷化合物，或其药物可接受的盐或前药，具有对存在于肠和肾中的钠依赖性葡萄糖共转运体2（SGLT2）的抑制活性；以及包含其作为活性成分的制药组合物，该组合物对预防或治疗代谢紊乱特别是糖尿病有用。