(napht-2-yl)methyl 2-azido-3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-allopyranoside | 1239365-04-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (napht-2-yl)methyl 2-azido-3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-allopyranoside
• CAS: 1239365-04-8
• 化学式: C₄₀H₄₁N₃O₆Si
• 分子量: 687.868
• InChiKey: JWWFTCCUJZRJEI-KZHDYJOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.92
• 重原子数：
  50.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  122.98
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  methyl 2-azido-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-allopyranoside 、 2-萘甲醇 在 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (napht-2-yl)methyl 2-azido-3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-α-D-allopyranoside 、 (napht-2-yl)methyl 2-azido-3-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-β-D-allopyranoside
  参考文献：
  名称：

  Biological Diversity from a Structurally Diverse Library: Systematically Scanning Conformational Space Using a Pyranose Scaffold

  摘要：

  Success in discovering bioactive peptide mimetics is often limited by the difficulties in correctly transposing known binding elements of the active peptide onto a small and metabolically more stable scaffold while maintaining bioactivity. Here we describe a scanning approach using a library of pyranose-based peptidomimetics that is structurally diverse in a systematic manner, designed to cover all possible conformations of tripeptide motifs containing two aromatic groups and one positive charge. Structural diversity was achieved by efficient selection of various chemoforms, characterized by a choice of pyranose scaffold of defined chirality and substitution pattern. A systematic scanning library of 490 compounds was thus designed, produced, and screened in vitro for activity at the somatostatin (sst(1-5)) and melanin-concentrating hormone (MCH1) receptors. Bioactive compounds were found for each target, with specific chemoform preferences identified in each case, which can be used to guide follow-on drug discovery projects without the need for scaffold hopping.

  DOI：

  10.1021/jm1002777