2-((3R,4S,5R)-3,4,5-Trihydroxy-tetrahydro-pyran-2-ylamino)-benzoic acid | 72921-42-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((3R,4S,5R)-3,4,5-Trihydroxy-tetrahydro-pyran-2-ylamino)-benzoic acid
• 英文别名: 2-[[(3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]amino]benzoic acid
• CAS: 72921-42-7
• 化学式: C₁₂H₁₅NO₆
• 分子量: 269.254
• InChiKey: TZQXBPJFWCSNDR-GZBOUJLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-((3R,4S,5R)-3,4,5-Trihydroxy-tetrahydro-pyran-2-ylamino)-benzoic acid 在 吡啶 作用下， 反应 48.0h， 以21%的产率得到N-<(acetoxycarbonyl)phenyl>-2,3,4-tri-O-acetyl-β-D-xylopyranosylamine
  参考文献：
  名称：

  Synthesis of N-(substituted phenyl)-D-xylopyranosylamines as potential modifiers of the formation of glycosaminoglycans

  摘要：

  N-(Substituted-phenyl)-D-xylopyranosylamines and their O-peracetyl derivatives have been synthesized and tested for their ability (a) to inhibit the replication of cultured B16 melanoma cells and (b) to modify the synthesis of glycosaminoglycans by these neoplastic cells. The most cytotoxic compound synthesized was N-(p-methoxyphenyl)-D-xylopyranosylamine (6), which produced 50% inhibition of cellular proliferation at a concentration of 2 microM; a number of other compounds were relatively cytotoxic, causing 50% inhibition of cell replication at levels of 12 to 25 microM. Several of the synthesized xylosides appeared to be capable of serving as artificial initiators of glycosaminoglycan synthesis, with the most active agents causing approximately 2- to 4-fold increases in the incorporation of [35S]sulfate into the glycosaminoglycans of B16 melanoma cells excreted into the culture medium.

  DOI：

  10.1021/jm00359a002
• 作为产物：
  描述：

  D-吡喃木糖 、 邻氨基苯甲酸 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 以43%的产率得到2-((3R,4S,5R)-3,4,5-Trihydroxy-tetrahydro-pyran-2-ylamino)-benzoic acid
  参考文献：
  名称：

  Synthesis of N-(substituted phenyl)-D-xylopyranosylamines as potential modifiers of the formation of glycosaminoglycans

  摘要：

  N-(Substituted-phenyl)-D-xylopyranosylamines and their O-peracetyl derivatives have been synthesized and tested for their ability (a) to inhibit the replication of cultured B16 melanoma cells and (b) to modify the synthesis of glycosaminoglycans by these neoplastic cells. The most cytotoxic compound synthesized was N-(p-methoxyphenyl)-D-xylopyranosylamine (6), which produced 50% inhibition of cellular proliferation at a concentration of 2 microM; a number of other compounds were relatively cytotoxic, causing 50% inhibition of cell replication at levels of 12 to 25 microM. Several of the synthesized xylosides appeared to be capable of serving as artificial initiators of glycosaminoglycan synthesis, with the most active agents causing approximately 2- to 4-fold increases in the incorporation of [35S]sulfate into the glycosaminoglycans of B16 melanoma cells excreted into the culture medium.

  DOI：

  10.1021/jm00359a002