1-((2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)ethanol | 1270018-02-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1-((2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)ethanol
• 英文别名: 1-[(2R,3S,4R,5S,6S)-6-[4-chloro-3-[[5-(furan-2-yl)-1,3-thiazol-2-yl]methyl]phenyl]-3,4,5-tris(phenylmethoxy)oxan-2-yl]ethanol
• CAS: 1270018-02-4
• 化学式: C₄₂H₄₀ClNO₆S
• 分子量: 722.302
• InChiKey: CJOUOQCHLOITPW-BKZOVOOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  51
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-((2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)ethanol 在 三氯化硼 作用下， 生成 (2S,3R,4R,5S,6R)-2-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-6-(1-hydroxyethyl)-tetrahydro-2H-pyran-3,4,5-triol
  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
• 作为产物：
  描述：

  ((2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)tetrahydro-2H-pyran-2-yl)methyl acetate 在 甲醇 、 sodium methylate 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-((2R,3S,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-((5-(furan-2-yl)thiazol-2-yl)methyl)phenyl)-tetrahydro-2H-pyran-2-yl)ethanol
  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

文献信息

• 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。
• US8586550B2
  申请人：——

  公开号：US8586550B2

  公开（公告）日：2013-11-19