(2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-(1-hydroxycyclopropyl)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol | 1185339-74-5

• 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-[4-chloro-3-[[4-(1-hydroxycyclopropyl)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1185339-74-5
• 化学式: C₂₂H₂₅ClO₆
• 分子量: 420.89
• InChiKey: AVABJDISDUSUOZ-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-[[2-chloro-5-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]methyl]benzoic acid 在 titanium(IV) isopropylate 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-(1-hydroxycyclopropyl)phenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  在4'-位取代的C-芳基糖苷作为有效的和选择性的肾钠依赖性葡萄糖共转运蛋白2（SGLT2）抑制剂，用于治疗2型糖尿病

  摘要：

  已经合成了一系列在远端芳基环的4'-位置具有各种取代基的C-芳基葡糖苷，并评估了其对hSGLT1和hSGLT2的抑制作用。发现在4'-位置处引入烷基或烷氧基取代基可提高SGLT2的效力，而在该位置处引入亲水性基团是有害的。具有烷氧基-，环烷氧基-或环烯氧基-乙氧基支架的化合物表现出良好的抑制活性和对SGLT2的高选择性。研究了所选化合物的体内功效。

  DOI：

  10.1016/j.bmcl.2011.06.032

文献信息

• Glucopyranosyl-substituted ((hetero)cycloalkylethynyl-benzyl)-benzene derivatives, medicaments containing such compounds, their use and process for their manufacture
  申请人：Himmelsbach Frank

  公开号：US20070027092A1

  公开（公告）日：2007-02-01

  Glucopyranosyl-substituted ((hetero)cycloalkylethynyl-benzyl)-benzene derivatives of the general formula I where the groups R 1 to R 6 as well as R 7a , R 7b , R 7c are defined according to claim 1 , including the tautomers, the stereoisomers thereof, the mixtures thereof and the salts thereof. The compounds according to the invention are suitable for the treatment of metabolic disorders.

  通用式I的葡萄糖吡喃基取代的((杂)环烷基乙炔基苄基)苯衍生物，其中基团R1至R6以及R7a、R7b、R7c根据权利要求1定义，包括其互变异构体、立体异构体、混合物及其盐。本发明的化合物适用于治疗代谢紊乱。
• METHODS FOR PREVENTING AND TREATING NEURODEGENERATIVE DISORDERS
  申请人：Wienrich Marion

  公开号：US20100081625A1

  公开（公告）日：2010-04-01

  The present invention relates to a method for treating, preventing or slowing, delaying or reversing progression of one or more neurodegenerative disorders in a patient in need thereof characterized by administering a glucopyranosyl-substituted benzene derivative, a tautomer, stereoisomer, mixture or salt thereof, as defined in claim 1 to the patient in need thereof.
• US7851602B2
  申请人：——

  公开号：US7851602B2

  公开（公告）日：2010-12-14
• C-Aryl glucosides substituted at the 4′-position as potent and selective renal sodium-dependent glucose co-transporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes
  作者：Baihua Xu、Yan Feng、Huawei Cheng、Yanli Song、Binhua Lv、Yuelin Wu、Congna Wang、Shengbin Li、Min Xu、Jiyan Du、Kun Peng、Jiajia Dong、Wenbin Zhang、Ting Zhang、Liangcheng Zhu、Haifeng Ding、Zelin Sheng、Ajith Welihinda、Jacques Y. Roberge、Brian Seed、Yuanwei Chen

  DOI：10.1016/j.bmcl.2011.06.032

  日期：2011.8

  Introduction of alkyl or alkoxy substituents at the 4′-position was found to improve SGLT2 potency, whereas introduction of a hydrophilic group at this position was deleterious. Compounds with alkoxy-, cycloalkoxy- or cycloalkenyloxy-ethoxy scaffolds exhibited good inhibitory activity and high selectivity toward SGLT2. Selected compounds were investigated for in vivo efficacy.

  已经合成了一系列在远端芳基环的4'-位置具有各种取代基的C-芳基葡糖苷，并评估了其对hSGLT1和hSGLT2的抑制作用。发现在4'-位置处引入烷基或烷氧基取代基可提高SGLT2的效力，而在该位置处引入亲水性基团是有害的。具有烷氧基-，环烷氧基-或环烯氧基-乙氧基支架的化合物表现出良好的抑制活性和对SGLT2的高选择性。研究了所选化合物的体内功效。