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 | 1072896-35-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: methyl (2R,4S,5R,6R)-4-acetyloxy-6-[(1R,2R)-1,2-diacetyloxy-3-azidopropyl]-5-[(2-phenylmethoxyacetyl)amino]-2-phenylsulfanyloxane-2-carboxylate
• CAS: 1072896-35-5
• 化学式: C₃₁H₃₆N₄O₁₁S
• 分子量: 672.713
• InChiKey: VBJWCDAEMGMYQX-YVJYRJHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  47
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  192
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  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 在 苯基硫三甲基硅烷 、 四丁基碘化铵 、 zinc(II) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Potent small molecule mouse CD22-inhibitors: Exploring the interaction of the residue at C-2 of sialic acid scaffold

  摘要：

  Our previous study revealed that compound 1 (9-(4'-hydroxy-4-biphenyl)acetamido-9-deoxy-Neu5Gc alpha 2-6GalOMP) has the most promising affinity for mCD22. Replacing the subterminal galactose residue of 1 with benzyl or biphenylmethyl as aglycone led to 38- and 20-fold higher potency, respectively. This discovery represents a new direction in inhibitor design suitable for pharmaceutical development. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.08.044
• 作为产物：
  描述：

  、 乙酸酐 在 吡啶 作用下， 反应 6.0h， 以6.88 g的产率得到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
  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