6-azide-1,2,3,4-tetra-O-benzoyl-6-deoxy-α-D-mannopyranose | 1609983-71-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-azide-1,2,3,4-tetra-O-benzoyl-6-deoxy-α-D-mannopyranose
• CAS: 1609983-71-2
• 化学式: C₃₄H₂₇N₃O₉
• 分子量: 621.603
• InChiKey: SGGPUFWNUKRGFK-LSPAEZJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  163.19
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  6-azide-1,2,3,4-tetra-O-benzoyl-6-deoxy-α-D-mannopyranose 在 potassium carbonate 、 三甲基膦 作用下， 以 四氢呋喃 为溶剂， 反应 125.0h， 生成 6-(2'-O-benzyl-phthalimido)-1,2,3,4-tetra-O-benzoyl-6-deoxy-α-D-mannopyranose
  参考文献：
  名称：

  Synthesis and evaluation of several oleanolic acid glycoconjugates as protein tyrosine phosphatase 1B inhibitors

  摘要：

  Sixteen novel oleanolic acid triterpenoid saponins were synthesized in an efficient and practical strategy, and their inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) and selectivity over T-cell protein tyrosine phosphatase (TCPTP) were evaluated in vitro. The preliminary structure activity relationship studies demonstrated that sugar-substituted moiety attached to the C-3 and C-28 positions of OA scaffold greatly affected the inhibitory activity against PTP1B and the selectivity over TCPTP. All the compounds showed inhibitory potencies, and compounds 1h, 1i and 1j exhibited remarkably potent inhibitory activities against PTP1B with IC50 values of 1.03, 0.78 and 3.12 mu M, respectively. More significantly, compound 1h showed greater than 4 folds selectivity over highly homologous TCPTP. In parallel, the lipophilicity evaluation of all synthesized compounds was tested as a prediction for pharmacological potency. According to the predicted log P values, the predicted Log P results showed that lipophilicity may correlate with the evaluated biological potency. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.080
• 作为产物：
  描述：

  1,2,3,4-Tetra-O-benzoyl-alpha-D-mannopyranose 在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酰氯 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 以63%的产率得到6-azide-1,2,3,4-tetra-O-benzoyl-6-deoxy-α-D-mannopyranose
  参考文献：
  名称：

  Synthesis and evaluation of several oleanolic acid glycoconjugates as protein tyrosine phosphatase 1B inhibitors

  摘要：

  Sixteen novel oleanolic acid triterpenoid saponins were synthesized in an efficient and practical strategy, and their inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) and selectivity over T-cell protein tyrosine phosphatase (TCPTP) were evaluated in vitro. The preliminary structure activity relationship studies demonstrated that sugar-substituted moiety attached to the C-3 and C-28 positions of OA scaffold greatly affected the inhibitory activity against PTP1B and the selectivity over TCPTP. All the compounds showed inhibitory potencies, and compounds 1h, 1i and 1j exhibited remarkably potent inhibitory activities against PTP1B with IC50 values of 1.03, 0.78 and 3.12 mu M, respectively. More significantly, compound 1h showed greater than 4 folds selectivity over highly homologous TCPTP. In parallel, the lipophilicity evaluation of all synthesized compounds was tested as a prediction for pharmacological potency. According to the predicted log P values, the predicted Log P results showed that lipophilicity may correlate with the evaluated biological potency. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.080