5-[(4-ethylphenyl)methyl]-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]pyridin-2-one | 842133-69-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[(4-ethylphenyl)methyl]-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]pyridin-2-one
• CAS: 842133-69-1
• 化学式: C₂₀H₂₅NO₆
• 分子量: 375.422
• InChiKey: AIGYAPPGIXCREG-XIKSMUEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  111
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-乙基苯基溴化镁 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 sodium hydride 、 一水合肼 、 乙二醇 、 1,2-二氯乙烷 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 5-[(4-ethylphenyl)methyl]-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]pyridin-2-one
  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

• 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.