6-(2-carboxynaphthyl) β-D-xylopyranoside | 1042924-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(2-carboxynaphthyl) β-D-xylopyranoside
• 英文别名: 6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxynaphthalene-2-carboxylic acid
• CAS: 1042924-52-6
• 化学式: C₁₆H₁₆O₇
• 分子量: 320.299
• InChiKey: KGENYWJMTNMTHU-CTASWTNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(2-carboxynaphthyl) β-D-xylopyranoside 、 L-丙氨酸甲酯盐酸盐 以65%的产率得到(2S)-2-[[6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxynaphthalene-2-carbonyl]amino]propanoic acid
  参考文献：
  名称：

  Xylosylated naphthoic acid–amino acid conjugates for investigation of glycosaminoglycan priming

  摘要：

  Three different series of xylosylated naphthoic acid-amino acid conjugates containing one or two amino acid residues were synthesized for the investigation of glycosaminoglycan priming and potential use as anti-tumor drugs. All xylosylated naphthoic acid-conjugates inhibited the growth of normal lung fibroblasts to some extent, whereas the growth of tumor derived T24 carcinoma cells was not affected. There was no correlation between amino acid conjugation, retention time and the antiproliferative activity. Only one compound initiated the priming of glycosaminoglycans. Modification of the naphthalene ring with one or two amino acid residues did not have any effect on proteoglycan biosynthesis or glycosaminoglycan priming in T24 carcinoma cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.006
• 作为产物：
  描述：

  6-羟基-2-萘甲酯 、 tetra-O-acetyl-β-D-xylopyranose 在 三氟化硼乙醚 、 三乙胺 、 sodium methylate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 22.75h， 以85%的产率得到6-(2-carboxynaphthyl) β-D-xylopyranoside
  参考文献：
  名称：

  Xylosylated naphthoic acid–amino acid conjugates for investigation of glycosaminoglycan priming

  摘要：

  Three different series of xylosylated naphthoic acid-amino acid conjugates containing one or two amino acid residues were synthesized for the investigation of glycosaminoglycan priming and potential use as anti-tumor drugs. All xylosylated naphthoic acid-conjugates inhibited the growth of normal lung fibroblasts to some extent, whereas the growth of tumor derived T24 carcinoma cells was not affected. There was no correlation between amino acid conjugation, retention time and the antiproliferative activity. Only one compound initiated the priming of glycosaminoglycans. Modification of the naphthalene ring with one or two amino acid residues did not have any effect on proteoglycan biosynthesis or glycosaminoglycan priming in T24 carcinoma cells. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.006

文献信息

• Xylosylated naphthoic acid–amino acid conjugates for investigation of glycosaminoglycan priming
  作者：Carl-Olof Abrahamsson、Ulf Ellervik、Johan Eriksson-Bajtner、Mårten Jacobsson、Katrin Mani

  DOI：10.1016/j.carres.2008.04.006

  日期：2008.7

  Three different series of xylosylated naphthoic acid-amino acid conjugates containing one or two amino acid residues were synthesized for the investigation of glycosaminoglycan priming and potential use as anti-tumor drugs. All xylosylated naphthoic acid-conjugates inhibited the growth of normal lung fibroblasts to some extent, whereas the growth of tumor derived T24 carcinoma cells was not affected. There was no correlation between amino acid conjugation, retention time and the antiproliferative activity. Only one compound initiated the priming of glycosaminoglycans. Modification of the naphthalene ring with one or two amino acid residues did not have any effect on proteoglycan biosynthesis or glycosaminoglycan priming in T24 carcinoma cells. (C) 2008 Elsevier Ltd. All rights reserved.