p-methoxyphenyl (methyl 4,7,8-tri-O-acetyl-9-azido-5-benzyloxyacetamido 3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->6)-2,3-di-O-benzoyl-β-D-galactopyranoside | 1072896-37-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: p-methoxyphenyl (methyl 4,7,8-tri-O-acetyl-9-azido-5-benzyloxyacetamido 3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->6)-2,3-di-O-benzoyl-β-D-galactopyranoside
• 英文别名: methyl (2R,4S,5R,6R)-4-acetyloxy-6-[(1R,2R)-1,2-diacetyloxy-3-azidopropyl]-2-[[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-3-hydroxy-6-(4-methoxyphenoxy)oxan-2-yl]methoxy]-5-[(2-phenylmethoxyacetyl)amino]oxane-2-carboxylate
• CAS: 1072896-37-7
• 化学式: C₅₂H₅₆N₄O₂₀
• 分子量: 1057.03
• InChiKey: NMVQNKYQISOBKR-SRAINISASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  76
• 可旋转键数：
  29
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  277
• 氢给体数：
  2
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl (methyl 4,7,8-tri-O-acetyl-9-azido-5-benzyloxyacetamido 3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->6)-2,3-di-O-benzoyl-β-D-galactopyranoside 在 lithium hydroxide monohydrate 、 乙醇 、 水 作用下， 反应 6.0h， 生成
  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：

  methyl (phenyl 4,7,8-tri-O-acetyl-9-azido-5-benzyloxyacetamido-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate 、 p-methoxyphenyl 2,3-di-O-benzoyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 16.33h， 生成 p-methoxyphenyl (methyl 4,7,8-tri-O-acetyl-9-azido-5-benzyloxyacetamido 3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->6)-2,3-di-O-benzoyl-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