4-α-D-mannopyranosylamino-benzoic acid | 86195-95-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-α-D-mannopyranosylamino-benzoic acid
• 英文别名: 4-α-D-Mannopyranosylamino-benzoesaeeure；4-D-Mannit-1-ylidenamino-benzoesaeure；4-[[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]benzoic acid
• CAS: 86195-95-1
• 化学式: C₁₃H₁₇NO₇
• 分子量: 299.28
• InChiKey: VXMVXDITZWJXJN-GCHJQGSQSA-N

物化性质

• 沸点：
  626.0±55.0 °C(predicted)
• 密度：
  1.622±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  140
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  D-甘露糖 、 对氨基苯甲酸 在 乙醇 、 溶剂黄146 作用下， 生成 4-α-D-mannopyranosylamino-benzoic acid
  参考文献：
  名称：

  N-(substituted-phenyl)-D-glycopyranosylamines and their O-acetyl derivatives as potential modifiers of the formation of glycosaminoglycans

  摘要：

  D-Arabinosyl, D-ribosyl, D-glucosyl, D-galactosyl, D-mannosyl, and L-rhamnosyl N-glycosides of p-aminobenzoic acid and their O-acetyl derivatives have been synthesized, and their ability to (a) inhibit the replication of cultured B16 melanoma cells and (b) modify the synthesis of glycosaminoglycans by these neoplastic cells have been evaluated. The most cytotoxic compound of the series was N-(p-carboxyphenyl)-2,3,4-tri-O-acetyl-D-arabinopyranosylamine (8), which produced 50% inhibition of cellular proliferation at a concentration of 4 microM; a number of other compounds were relatively cytotoxic, causing 50% inhibition of cell replication at levels of 18 to 49 microM. These effects were not due to modification of glycosaminoglycan biosynthesis, since these compounds were ineffective as inhibitors or initiators of the formation of these macromolecules.

  DOI：

  10.1021/jm00363a020

文献信息

• N-(substituted-phenyl)-D-glycopyranosylamines and their O-acetyl derivatives as potential modifiers of the formation of glycosaminoglycans
  作者：Lin Wang、Charles A. Maniglia、Sharon L. Mella、Alan C. Sartorelli

  DOI：10.1021/jm00363a020

  日期：1983.9

  D-Arabinosyl, D-ribosyl, D-glucosyl, D-galactosyl, D-mannosyl, and L-rhamnosyl N-glycosides of p-aminobenzoic acid and their O-acetyl derivatives have been synthesized, and their ability to (a) inhibit the replication of cultured B16 melanoma cells and (b) modify the synthesis of glycosaminoglycans by these neoplastic cells have been evaluated. The most cytotoxic compound of the series was N-(p-carboxyphenyl)-2,3,4-tri-O-acetyl-D-arabinopyranosylamine (8), which produced 50% inhibition of cellular proliferation at a concentration of 4 microM; a number of other compounds were relatively cytotoxic, causing 50% inhibition of cell replication at levels of 18 to 49 microM. These effects were not due to modification of glycosaminoglycan biosynthesis, since these compounds were ineffective as inhibitors or initiators of the formation of these macromolecules.