p-methoxyphenyl (9-amino-3,5,9-trideoxy-5-glycolamido-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside | 1072896-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl (9-amino-3,5,9-trideoxy-5-glycolamido-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside
• 英文别名: GSC-633；NeuGc9N(a2-6)Gal(b)-O-Ph(4-OMe)；(2R,4S,5R,6R)-6-[(1R,2R)-3-amino-1,2-dihydroxypropyl]-4-hydroxy-5-[(2-hydroxyacetyl)amino]-2-[[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methoxyphenoxy)oxan-2-yl]methoxy]oxane-2-carboxylic acid
• CAS: 1072896-39-9
• 化学式: C₂₄H₃₆N₂O₁₅
• 分子量: 592.554
• InChiKey: VWHDAPLZPAOSHZ-OUIOXYPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.5
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  280
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl (9-amino-3,5,9-trideoxy-5-glycolamido-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside 、 3,5-二甲氧基苯甲醛 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 反应 51.0h， 以75%的产率得到p-methoxyphenyl (3,5,9-trideoxy-5-glycolamido-9-(3,5-dimethoxybenzyl)amino-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside
  参考文献：
  名称：

  Design, Synthesis, and Structure−Affinity Relationships of Novel Series of Sialosides as CD22-Specific Inhibitors

  摘要：

  Sialosides incorporating substituted amides or amines at 9-position of sialic acid moiety have been synthesized and evaluated as CD22 inhibitors. Several derivatives exhibited inhibitory potency in sub- to low micromolar range (e. g., 8o, 9d, 9g, and 9k showed IC50 values 0.40, 0.47, 0.24, and 0.23 mu M, respectively, for hCD22, while 8p. 8q, and 9f, showed IC50 values 1.70, 2.90, and 4.10 mu M, respectively, for mCD22). The most significant result was the strongly enhanced affinity of 9g and 9k containing 9-(2' or 4'-hydroxy-4-biphenyl) methylamino substituents (600-fold more potent for hCD22 than the corresponding 9-hydroxy derivative; 7a). Molecular modeling study was carried out to get some insights into the molecular basis of CD22 inhibition. To the best of our knowledge, this is the first systematic structure-affinity relationship study on inhibition of CD22.

  DOI：

  10.1021/jm8000696
• 作为产物：
  描述：

  在 palladium hydroxide on carbon 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 p-methoxyphenyl (9-amino-3,5,9-trideoxy-5-glycolamido-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside
  参考文献：
  名称：

  Design, Synthesis, and Structure−Affinity Relationships of Novel Series of Sialosides as CD22-Specific Inhibitors

  摘要：

  Sialosides incorporating substituted amides or amines at 9-position of sialic acid moiety have been synthesized and evaluated as CD22 inhibitors. Several derivatives exhibited inhibitory potency in sub- to low micromolar range (e. g., 8o, 9d, 9g, and 9k showed IC50 values 0.40, 0.47, 0.24, and 0.23 mu M, respectively, for hCD22, while 8p. 8q, and 9f, showed IC50 values 1.70, 2.90, and 4.10 mu M, respectively, for mCD22). The most significant result was the strongly enhanced affinity of 9g and 9k containing 9-(2' or 4'-hydroxy-4-biphenyl) methylamino substituents (600-fold more potent for hCD22 than the corresponding 9-hydroxy derivative; 7a). Molecular modeling study was carried out to get some insights into the molecular basis of CD22 inhibition. To the best of our knowledge, this is the first systematic structure-affinity relationship study on inhibition of CD22.

  DOI：

  10.1021/jm8000696