(2S,3R,4R,5S,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triol | 1338728-27-0

• 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-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: (2S,3R,4R,5S,6R)-2-(2-(Allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triol；(2S,3R,4R,5S,6R)-2-[4-chloro-5-[(4-ethoxyphenyl)methyl]-2-prop-2-enoxyphenyl]-6-(prop-2-enoxymethyl)oxane-3,4,5-triol
• CAS: 1338728-27-0
• 化学式: C₂₇H₃₃ClO₇
• 分子量: 505.008
• InChiKey: RNTIJIRUHGUUGV-SEFGFODJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5S,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triol 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 90.0h， 生成 (8R,9R,10R,11S,12S)-9,10,11-tris(acetyloxy)-15-chloro-14-(4-ethoxybenzyl)-5,7,8,9,10,11,12-heptahydro-2H-8,12-epoxybenzo[g][1,6]dioxacyclotetradecine
  参考文献：
  名称：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents

  摘要：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors were designed and synthesized. Two different synthetic routes of macrocyclization were adopted to prepare novel ansa SGLT2 inhibitors. Among the compounds tested, [1,7]dioxacyclopentadecine macrocycles possessing methylthiophenyl at the distal ring 40 or ethoxyphenyl at the distal ring 23 showed the best in vitro inhibitory activity in this series to date (40, IC50 = 0.778 nM and 23, IC50 = 0.899 nM) against hSGLT2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.045
• 作为产物：
  描述：

  (3R,4S,5S,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol 在 吡啶 、 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟甲磺酸 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 sodium methylate 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 26.5h， 生成 (2S,3R,4R,5S,6R)-2-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-6-(allyloxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents

  摘要：

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors were designed and synthesized. Two different synthetic routes of macrocyclization were adopted to prepare novel ansa SGLT2 inhibitors. Among the compounds tested, [1,7]dioxacyclopentadecine macrocycles possessing methylthiophenyl at the distal ring 40 or ethoxyphenyl at the distal ring 23 showed the best in vitro inhibitory activity in this series to date (40, IC50 = 0.778 nM and 23, IC50 = 0.899 nM) against hSGLT2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.045

文献信息

• NOVEL C-ARYL ANSA SGLT2 INHIBITORS
  申请人：Kim Min Ju

  公开号：US20140213642A1

  公开（公告）日：2014-07-31

  Disclosed is a novel C-aryl ansa compound 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. Also provided are a method for preparing the compound, and a method for preventing or treating metabolic disorders, particularly diabetes, by using the compound.

  本发明涉及一种新的C-芳基ansa化合物，具有抑制肠和肾中存在的钠依赖性葡萄糖转运蛋白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，该组合物对预防或治疗代谢紊乱，特别是糖尿病有用。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紊乱，特别是糖尿病的方法。
• C-aryl ansa SGLT2 inhibitors
  申请人：Kim Min Ju

  公开号：US08921412B2

  公开（公告）日：2014-12-30

  Disclosed is a novel C-aryl ansa compound 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. Also provided are a method for preparing the compound, and a method for preventing or treating metabolic disorders, particularly diabetes, by using the compound.

  本发明公开了一种新的C-芳基ansa化合物，其具有对存在于肠和肾中的钠依赖性葡萄糖转运蛋白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，可用于预防或治疗代谢性疾病，特别是糖尿病。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，特别是糖尿病的方法。
• US8921412B2
  申请人：——

  公开号：US8921412B2

  公开（公告）日：2014-12-30
• [EN] NOVEL C-ARYL ANSA SGLT2 INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS C-ARYLE ANSA DE SGLT2
  申请人：GREEN CROSS CORP

  公开号：WO2012173410A2

  公开（公告）日：2012-12-20

  The present invention relates to a novel C-aryl ansa compound 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.
• Novel macrocyclic C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents
  作者：Min Ju Kim、Suk Ho Lee、So Ok Park、Hyunku Kang、Jun Sung Lee、Ki Nam Lee、Myung Eun Jung、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmc.2011.07.045

  日期：2011.9

  Novel macrocyclic C-aryl glucoside SGLT2 inhibitors were designed and synthesized. Two different synthetic routes of macrocyclization were adopted to prepare novel ansa SGLT2 inhibitors. Among the compounds tested, [1,7]dioxacyclopentadecine macrocycles possessing methylthiophenyl at the distal ring 40 or ethoxyphenyl at the distal ring 23 showed the best in vitro inhibitory activity in this series to date (40, IC50 = 0.778 nM and 23, IC50 = 0.899 nM) against hSGLT2. (C) 2011 Elsevier Ltd. All rights reserved.