(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-(bromomethyl)-5-chlorothiophen-2-yl)tetrahydro-2H-pyran | 1344027-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-(bromomethyl)-5-chlorothiophen-2-yl)tetrahydro-2H-pyran
• 英文别名: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-(bromomethyl)-5-chlorothiophen-2-yl)-tetrahydro-2H-pyran；(2R,3R,4S,5R,6R)-2-[4-(bromomethyl)-5-chlorothiophen-2-yl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 1344027-66-2
• 化学式: C₃₉H₃₈BrClO₅S
• 分子量: 734.151
• InChiKey: WGQPFHIDFXJCAY-MUIHICNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  74.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-(bromomethyl)-5-chlorothiophen-2-yl)tetrahydro-2H-pyran 在 甲醇 、 四(三苯基膦)钯 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 caesium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 3.0h， 生成 (2R,3R,4S,5S,6R)-2-(5-chloro-4-(4-methylbenzyl)thiophen-2-yl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
  参考文献：
  名称：

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

  摘要：

  Novel thiophene C-aryl glucoside SGLT2 inhibitors were designed and synthesized. Two different types of thiophene derivatives were readily prepared. Among the compounds tested, ethylphenyl at the distal ring 71p showed the best in vitro inhibitory activity in this series to date (IC50=4.47 nM) against SGLT2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.014
• 作为产物：
  描述：

  (5-bromo-2-chlorothiophen-3-yl)methanol 在 吡啶 咪唑 、 三乙基硅烷 、 4-二甲氨基吡啶 、 正丁基锂 、 lithium hydroxide monohydrate 、 三氟化硼乙醚 、 四丁基氟化铵 、 水 、 三溴化磷 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.17h， 生成 (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(4-(bromomethyl)-5-chlorothiophen-2-yl)tetrahydro-2H-pyran
  参考文献：
  名称：

  [EN] NOVEL THIOPHENE DERIVATIVE AS SGLT2 INHIBITOR AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  [FR] NOUVEAU DÉRIVÉ DU THIOPHÈNE UTILISÉ COMME INHIBITEUR DU SGLT2 ET COMPOSITION PHARMACEUTIQUE COMPRENANT CE DÉRIVÉ

  摘要：

  公开号：

  WO2012033390A3

文献信息

• NOVEL THIOPHENE DERIVATIVE AS SGLT2 INHIBITOR AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  申请人：Lee Jinhwa

  公开号：US20130172278A1

  公开（公告）日：2013-07-04

  The present invention relates to a novel compound with thiophene 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. The prevention also provides a method for preparing same, a pharmaceutical composition containing same, and a method for preventing or treating metabolic disorders, particularly diabetes.

  本发明涉及一种具有噻吩环的新化合物，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，并且包含该化合物作为活性成分的药物组合物，该组合物有助于预防或治疗代谢性疾病，特别是糖尿病。预防还提供了制备该化合物的方法，含有该化合物的药物组合物以及预防或治疗代谢性疾病，特别是糖尿病的方法。
• Thiophene derivative as SGLT2 inhibitor and pharmaceutical composition comprising same
  申请人：Lee Jinhwa

  公开号：US09006187B2

  公开（公告）日：2015-04-14

  The present invention relates to a novel compound with thiophene 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. The prevention also provides a method for preparing same, a pharmaceutical composition containing same, and a method for preventing or treating metabolic disorders, particularly diabetes.

  本发明涉及一种新型含有噻吩环的化合物，该化合物具有抑制肠道和肾脏中存在的钠依赖性葡萄糖转运蛋白2（SGLT2）的活性，并且包括该化合物作为活性成分的制药组合物，该组合物有助于预防或治疗代谢性疾病，特别是糖尿病。本发明还提供了制备该化合物的方法，含有该化合物的制药组合物，以及预防或治疗代谢性疾病，特别是糖尿病的方法。
• US9006187B2
  申请人：——

  公开号：US9006187B2

  公开（公告）日：2015-04-14
• [EN] NOVEL THIOPHENE DERIVATIVE AS SGLT2 INHIBITOR AND PHARMACEUTICAL COMPOSITION COMPRISING SAME<br/>[FR] NOUVEAU DÉRIVÉ DU THIOPHÈNE UTILISÉ COMME INHIBITEUR DU SGLT2 ET COMPOSITION PHARMACEUTIQUE COMPRENANT CE DÉRIVÉ
  申请人：GREEN CROSS CORP

  公开号：WO2012033390A3

  公开（公告）日：2012-05-18
• Novel thiophenyl C-aryl glucoside SGLT2 inhibitors as potential antidiabetic agents
  作者：Suk Ho Lee、Kwang-Seop Song、Jong Yup Kim、Misuk Kang、Jun Sung Lee、Seung-Hwan Cho、Hyun-Ju Park、Jeongmin Kim、Jinhwa Lee

  DOI：10.1016/j.bmc.2011.08.014

  日期：2011.10

  Novel thiophene C-aryl glucoside SGLT2 inhibitors were designed and synthesized. Two different types of thiophene derivatives were readily prepared. Among the compounds tested, ethylphenyl at the distal ring 71p showed the best in vitro inhibitory activity in this series to date (IC50=4.47 nM) against SGLT2. (C) 2011 Elsevier Ltd. All rights reserved.