(2S,3S,4S,5R,6R)-6-[2-(2,5-Dioxo-pyrrolidin-1-yl)-ethoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4S,5R,6R)-6-[2-(2,5-Dioxo-pyrrolidin-1-yl)-ethoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid
• 英文别名: (2S,3S,4S,5R,6R)-6-[2-(2,5-dioxopyrrolidin-1-yl)ethoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• 化学式: C₁₂H₁₇NO₉
• 分子量: 319.268
• InChiKey: LFUIYDRRVKIESD-GOVZDWNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[2-(2,5-dioxo-pyrrolidin-1-yl)-ethoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester 在 甲醇 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S,4S,5R,6R)-6-[2-(2,5-Dioxo-pyrrolidin-1-yl)-ethoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Identification of novel inhibitors of fibroblast growth factor (FGF-2) binding to heparin and endothelial cell survival from a structurally diverse carbohybrid library

  摘要：

  Inhibitors of FGF-2 binding to a heparin-albumin conjugate were identified by ELISA from a library of glucuronic acid derivatives. These compounds were also inhibitors of endothelial cell survival that is dependant on FGF-2 and heparin or heparan sulfate proteoglycans. The results indicate that these bioactive compounds may prove useful as lead structures for the further development of pharmaceutical agents capable of modulating biological activity of FGF-2. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00700-x

文献信息

• [EN] MONOSACCHARIDE DERIVATIVES<br/>[FR] DERIVES DE MONOSACCHARIDES
  申请人：UNIV DUBLIN

  公开号：WO2003018598A2

  公开（公告）日：2003-03-06

  Monosaccharide (pyranoside) conjugates of the formula have been found to be useful as enhancers and/or inhibitors of heparin binding to FGF. The compounds have the potential to be useful in regenerative medicine or for treatment of pathological disease associated with FGF activity or as glycoprocessing inhibitors. In particular the compounds are potential modulators of fibroblast growth factors (FGFs) and fibronectin, as mitogenic agents and as inhibitors of endothelial cell survival.
• Identification of novel inhibitors of fibroblast growth factor (FGF-2) binding to heparin and endothelial cell survival from a structurally diverse carbohybrid library
  作者：Paul V Murphy、Nigel Pitt、Alan O'Brien、Philomena M Enright、Amanda Dunne、Stephen J Wilson、Rhona M Duane、Kathy M O'Boyle

  DOI：10.1016/s0960-894x(02)00700-x

  日期：2002.11

  Inhibitors of FGF-2 binding to a heparin-albumin conjugate were identified by ELISA from a library of glucuronic acid derivatives. These compounds were also inhibitors of endothelial cell survival that is dependant on FGF-2 and heparin or heparan sulfate proteoglycans. The results indicate that these bioactive compounds may prove useful as lead structures for the further development of pharmaceutical agents capable of modulating biological activity of FGF-2. (C) 2002 Elsevier Science Ltd. All rights reserved.