methyl 3-(N-β-D-glucopyranosyl-carbamoyl)benzoate | 896730-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-(N-β-D-glucopyranosyl-carbamoyl)benzoate
• 英文别名: methyl 3-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]carbamoyl]benzoate
• CAS: 896730-92-0
• 化学式: C₁₅H₁₉NO₈
• 分子量: 341.318
• InChiKey: LZNHHRBNVXOOMK-YGEZULPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3-(N-β-D-glucopyranosyl-carbamoyl)benzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以99%的产率得到3-(N-β-D-glucopyranosyl-carbamoyl)benzoic acid
  参考文献：
  名称：

  Synthesis of N-(β-d-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase

  摘要：

  O-Peracetylated N-(beta-D-glucopyranosyl)imino trimethylphosphorane obtained in situ from 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide and PMe3 was reacted with saturated and unsaturated aliphatic and aromatic dicarboxylic acids, or their anhydrides. or monoesters to give the corresponding N-(beta-D-glucopyranosyl) monoamides of dicarboxylic acids or derivatives. The acetyl protecting groups were removed according to the Zemplen protocol to give a series of compounds which showed moderate inhibitory effects against rabbit muscle glycogen phosphorylase b. The best inhibitor was 3-(N-beta-D-glucopyranosyl-carbamoy)propanoic acid (7) with K-i = 20 mu M. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.002
• 作为产物：
  描述：

  [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(trimethyl-lambda5-phosphanylidene)amino]oxan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 methyl 3-(N-β-D-glucopyranosyl-carbamoyl)benzoate
  参考文献：
  名称：

  Synthesis of N-(β-d-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase

  摘要：

  O-Peracetylated N-(beta-D-glucopyranosyl)imino trimethylphosphorane obtained in situ from 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide and PMe3 was reacted with saturated and unsaturated aliphatic and aromatic dicarboxylic acids, or their anhydrides. or monoesters to give the corresponding N-(beta-D-glucopyranosyl) monoamides of dicarboxylic acids or derivatives. The acetyl protecting groups were removed according to the Zemplen protocol to give a series of compounds which showed moderate inhibitory effects against rabbit muscle glycogen phosphorylase b. The best inhibitor was 3-(N-beta-D-glucopyranosyl-carbamoy)propanoic acid (7) with K-i = 20 mu M. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.002

文献信息

• Synthesis of N-(β-d-glucopyranosyl) monoamides of dicarboxylic acids as potential inhibitors of glycogen phosphorylase
  作者：Katalin Czifrák、Zsuzsa Hadady、Tibor Docsa、Pál Gergely、Jürgen Schmidt、Ludger Wessjohann、László Somsák

  DOI：10.1016/j.carres.2006.03.002

  日期：2006.6

  O-Peracetylated N-(beta-D-glucopyranosyl)imino trimethylphosphorane obtained in situ from 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide and PMe3 was reacted with saturated and unsaturated aliphatic and aromatic dicarboxylic acids, or their anhydrides. or monoesters to give the corresponding N-(beta-D-glucopyranosyl) monoamides of dicarboxylic acids or derivatives. The acetyl protecting groups were removed according to the Zemplen protocol to give a series of compounds which showed moderate inhibitory effects against rabbit muscle glycogen phosphorylase b. The best inhibitor was 3-(N-beta-D-glucopyranosyl-carbamoy)propanoic acid (7) with K-i = 20 mu M. (c) 2006 Elsevier Ltd. All rights reserved.