(2R,3R,4S,5S,6R)-2-[3-[(4-ethylphenyl)methyl]indazol-2-yl]-6-(hydroxymethyl)oxane-3,4,5-triol | 842133-72-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (2R,3R,4S,5S,6R)-2-[3-[(4-ethylphenyl)methyl]indazol-2-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 842133-72-6
• 化学式: C₂₂H₂₆N₂O₅
• 分子量: 398.459
• InChiKey: DDIMTYMXZBVVRO-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  C₂₁H₂₄N₂O₂ 在 sodium methylate 作用下， 以 乙腈 为溶剂， 生成 (2R,3R,4S,5S,6R)-2-[3-[(4-ethylphenyl)methyl]indazol-2-yl]-6-(hydroxymethyl)oxane-3,4,5-triol 、 (2R,3R,4S,5S,6R)-2-[3-[(4-ethylphenyl)methyl]indazol-1-yl]-6-(hydroxymethyl)oxane-3,4,5-triol
  参考文献：
  名称：

  N-glucosides as human sodium-dependent glucose cotransporter 2 (hSGLT2) inhibitors

  摘要：

  Inhibition of renal sodium-dependent glucose cotransporter 2 (SGLT2) increases urinary glucose excretion (UGE), and thus reduces blood glucose levels in hyperglycemia. A series of N-glucosides was synthesized for biological evaluation as human SGLT2 (hSGLT2) inhibitors. Among these compounds, N-glucoside 9d possessing an indole core structure showed good in vitro activity (IC50 = 7.1 nM against hSGLT2). Furthermore, 9d exhibited favorable in vivo potency with regard to UGE in rats based on good pharmacokinetic profiles. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.042

文献信息

• GLUCOPYRANOSIDE COMPOUND
  申请人：NOMURA Sumihiro

  公开号：US20110105424A1

  公开（公告）日：2011-05-05

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH 2 ) n — (n is 1 or 2); or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  该化合物的化学式为：其中环A和环B为：（1）环A为可选取代的不饱和单环杂环环，环B为可选取代的不饱和单环杂环环，可选取代的不饱和融合杂双环环或可选取代的苯环，（2）环A为可选取代的苯环，环B为可选取代的不饱和单环杂环环或可选取代的不饱和融合杂双环环，或（3）环A为可选取代的不饱和融合杂双环环，环B独立地为可选取代的不饱和单环杂环环，可选取代的不饱和融合杂双环环或可选取代的苯环；X为碳原子或氮原子；Y为—（CH2）n—（n为1或2）；或其药学上可接受的盐或前药。
• Novel compounds having inhibitory activity against sodium-dependant glucose transporter
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP2514756A1

  公开（公告）日：2012-10-24

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is ―(CH2)n-(n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  式中的化合物： 其中环 A 和环 B 是(1) 环 A 是被任选取代的不饱和单环杂环，环 B 是被任选取代的不饱和单环杂环、被任选取代的不饱和融合杂环或被任选取代的苯环环 B 是任选取代的不饱和单环杂环或任选取代的不饱和融合杂环，或 (3) 环 A 是任选取代的不饱和融合杂环，环 B 独立地是任选取代的不饱和单环杂环、任选取代的不饱和融合杂环或任选取代的苯环；X 是碳原子或氮原子； Y 是-(CH2)n-(n 是 1 或 2)； 其药学上可接受的盐，或其原药。
• NOVEL COMPOUNDS HAVING INHIBITORY ACTIVITY AGAINST SODIUM-DEPENDANT GLUCOSE TRANSPORTER
  申请人：Mitsubishi Tanabe Pharma Corporation

  公开号：EP2514756B1

  公开（公告）日：2014-12-17
• US8202984B2
  申请人：——

  公开号：US8202984B2

  公开（公告）日：2012-06-19
• N-glucosides as human sodium-dependent glucose cotransporter 2 (hSGLT2) inhibitors
  作者：Yasuo Yamamoto、Eiji Kawanishi、Yuichi Koga、Shigeki Sakamaki、Toshiaki Sakamoto、Kiichiro Ueta、Yasuaki Matsushita、Chiaki Kuriyama、Minoru Tsuda-Tsukimoto、Sumihiro Nomura

  DOI：10.1016/j.bmcl.2013.08.042

  日期：2013.10

  Inhibition of renal sodium-dependent glucose cotransporter 2 (SGLT2) increases urinary glucose excretion (UGE), and thus reduces blood glucose levels in hyperglycemia. A series of N-glucosides was synthesized for biological evaluation as human SGLT2 (hSGLT2) inhibitors. Among these compounds, N-glucoside 9d possessing an indole core structure showed good in vitro activity (IC50 = 7.1 nM against hSGLT2). Furthermore, 9d exhibited favorable in vivo potency with regard to UGE in rats based on good pharmacokinetic profiles. (C) 2013 Elsevier Ltd. All rights reserved.