methyl 3-O-[4-(3-(1-methylindol-3-yl)prop-1-ynyl)benzyl]-β-D-galactopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-[4-(3-(1-methylindol-3-yl)prop-1-ynyl)benzyl]-β-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-methoxy-4-[[4-[3-(1-methylindol-3-yl)prop-1-ynyl]phenyl]methoxy]oxane-3,5-diol
• 化学式: C₂₆H₂₉NO₆
• 分子量: 451.519
• InChiKey: DGSPQKRZVLUGRW-UVIRKTLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  93.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 吡啶 、 sodium methylate 、 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 methyl 3-O-[4-(3-(1-methylindol-3-yl)prop-1-ynyl)benzyl]-β-D-galactopyranoside
  参考文献：
  名称：

  Cobalt-mediated solid phase synthesis of 3-O-alkynylbenzyl galactosides and their evaluation as galectin inhibitors

  摘要：

  Methyl beta-D-galactoside was converted to the corresponding 3,4-O-stannylene acetal, which was selectively benzylated with 3-iodobenzyl bromide and coupled to a polymer-bound propargylic ether via a Sonogashira reaction. The polymer-bound carbohydrate substrate was cleaved from the resin with different carbon nucleophiles in a cobalt-mediated Nicholas reaction. The product 3-O-alkynylbenzyl galactosides were screened towards galectin-1, -3, -7, -8N and -9N in a competitive fluorescence polarisation assay. Particularly potent inhibitors were identified against galectin-7 with affinity enhancements up to one order of magnitude due to the 3-O-alkynylbenzyl moiety. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.057

文献信息

• Cobalt-mediated solid phase synthesis of 3-O-alkynylbenzyl galactosides and their evaluation as galectin inhibitors
  作者：Anders Bergh、Hakon Leffler、Anders Sundin、Ulf J. Nilsson、Nina Kann

  DOI：10.1016/j.tet.2006.06.057

  日期：2006.8

  Methyl beta-D-galactoside was converted to the corresponding 3,4-O-stannylene acetal, which was selectively benzylated with 3-iodobenzyl bromide and coupled to a polymer-bound propargylic ether via a Sonogashira reaction. The polymer-bound carbohydrate substrate was cleaved from the resin with different carbon nucleophiles in a cobalt-mediated Nicholas reaction. The product 3-O-alkynylbenzyl galactosides were screened towards galectin-1, -3, -7, -8N and -9N in a competitive fluorescence polarisation assay. Particularly potent inhibitors were identified against galectin-7 with affinity enhancements up to one order of magnitude due to the 3-O-alkynylbenzyl moiety. (c) 2006 Elsevier Ltd. All rights reserved.