(R(S))-2-phenylethyl α-d-mannopyranosyl sulfoxide | 1279712-22-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R(S))-2-phenylethyl α-d-mannopyranosyl sulfoxide
• 英文别名: (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[(R)-2-phenylethylsulfinyl]oxane-3,4,5-triol
• CAS: 1279712-22-9
• 化学式: C₁₄H₂₀O₆S
• 分子量: 316.375
• InChiKey: MXSSIIJFICBNQB-VHJDCMPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-苯乙硫醇 在 甲醇 、 三氟化硼乙醚 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (R(S))-2-phenylethyl α-d-mannopyranosyl sulfoxide
  参考文献：
  名称：

  α-d-Mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II

  摘要：

  Human Golgi alpha-mannosidase II (hGM) is a pharmaceutical target for the design of inhibitors with antitumor activity. Nanomolar inhibitors of hGM exhibit unwanted co-inhibition of the human lysosomal alpha-mannosidase (hLM). Hence, improving specificity of the inhibitors directed toward hGM is desired in order to use them in cancer chemotherapy. We report on the rapid synthesis of D-mannose derivatives having one of the RS-. R(SO)- or R(SO(2))- groups at the alpha-anomeric position. Inhibitory properties of thirteen synthesized alpha-D-mannopyranosides were tested against the recombinant enzyme Drosophila melanogaster homolog of hGM (dGMIIb) and hLM (dLM408). Derivatives with the sulfonyl [R(SO(2))-] group exhibited inhibitory activities at the mM level toward both dGMIIb (IC(50) = 1.5-2.5 mM) and dLM408 (IC(50) = 1.0-2.0 mM). Among synthesized, only the benzylsulfonyl derivative showed selectivity toward dGMIIb. Its inhibitory activity was explained based on structural analysis of the built 3-D complexes of the enzyme with the docked compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.012

文献信息

• α-d-Mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II
  作者：Monika Poláková、Sergej Šesták、Erika Lattová、Ladislav Petruš、Ján Mucha、Igor Tvaroška、Juraj Kóňa

  DOI：10.1016/j.ejmech.2011.01.012

  日期：2011.3

  Human Golgi alpha-mannosidase II (hGM) is a pharmaceutical target for the design of inhibitors with antitumor activity. Nanomolar inhibitors of hGM exhibit unwanted co-inhibition of the human lysosomal alpha-mannosidase (hLM). Hence, improving specificity of the inhibitors directed toward hGM is desired in order to use them in cancer chemotherapy. We report on the rapid synthesis of D-mannose derivatives having one of the RS-. R(SO)- or R(SO(2))- groups at the alpha-anomeric position. Inhibitory properties of thirteen synthesized alpha-D-mannopyranosides were tested against the recombinant enzyme Drosophila melanogaster homolog of hGM (dGMIIb) and hLM (dLM408). Derivatives with the sulfonyl [R(SO(2))-] group exhibited inhibitory activities at the mM level toward both dGMIIb (IC(50) = 1.5-2.5 mM) and dLM408 (IC(50) = 1.0-2.0 mM). Among synthesized, only the benzylsulfonyl derivative showed selectivity toward dGMIIb. Its inhibitory activity was explained based on structural analysis of the built 3-D complexes of the enzyme with the docked compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.