N-(β-D-glucopyranosyl) 3-(2-naphthyl)-propenoic amide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(β-D-glucopyranosyl) 3-(2-naphthyl)-propenoic amide
• 英文别名: (E)-3-naphthalen-2-yl-N-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]prop-2-enamide
• 化学式: C₁₉H₂₁NO₆
• 分子量: 359.379
• InChiKey: WOGKJCFYMGJORG-XBXJFLBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (E)-3-(萘-2-基)丙烯酸 在 sodium methylate 、 三甲基膦 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 生成 N-(β-D-glucopyranosyl) 3-(2-naphthyl)-propenoic amide
  参考文献：
  名称：

  Synthesis of N-(β-D-glucopyranosyl)- and N-(2-acetamido-2-deoxy-β-D-glucopyranosyl) amides as inhibitors of glycogen phosphorylase

  摘要：

  2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl- and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl azides were transformed into the corresponding per-O-acetylated N-(beta-D-glycopyranosyl) amides via a PMe3 mediated Staudinger protocol (generation of N-(beta-D-glycopyranosyl)imino-trimethylphosphoranes followed by acylation with carboxylic acids, acid chlorides or anhydrides). The deprotected compounds obtained by Zemplen deacetylation were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitor of this series has been N-(beta-D-glucopyranosyl) 3-(2-naphthyl)-propenoic amide (K-i = 3.5 muM). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.013

文献信息

• Synthesis of N-(β-D-glucopyranosyl)- and N-(2-acetamido-2-deoxy-β-D-glucopyranosyl) amides as inhibitors of glycogen phosphorylase
  作者：Zoltán Györgydeák、Zsuzsa Hadady、Nóra Felföldi、Attila Krakomperger、Veronika Nagy、Marietta Tóth、Attila Brunyánszki、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.bmc.2004.07.013

  日期：2004.9

  2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl- and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl azides were transformed into the corresponding per-O-acetylated N-(beta-D-glycopyranosyl) amides via a PMe3 mediated Staudinger protocol (generation of N-(beta-D-glycopyranosyl)imino-trimethylphosphoranes followed by acylation with carboxylic acids, acid chlorides or anhydrides). The deprotected compounds obtained by Zemplen deacetylation were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitor of this series has been N-(beta-D-glucopyranosyl) 3-(2-naphthyl)-propenoic amide (K-i = 3.5 muM). (C) 2004 Elsevier Ltd. All rights reserved.