cinnamyl 6-O-α-D-mannopyranosyl-1-thio-α-D-mannopyranoside | 101648-51-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cinnamyl 6-O-α-D-mannopyranosyl-1-thio-α-D-mannopyranoside
• 英文别名: (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-[(E)-3-phenylprop-2-enyl]sulfanyloxan-2-yl]methoxy]oxane-3,4,5-triol
• CAS: 101648-51-5
• 化学式: C₂₁H₃₀O₁₀S
• 分子量: 474.529
• InChiKey: ZEPXHCNTEQEMKJ-DDRWJXPDSA-N

物化性质

• 沸点：
  777.1±60.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  195
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-O-(tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranosyl bromide 在 potassium disulphite 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 11.0h， 生成 cinnamyl 6-O-α-D-mannopyranosyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Inhibition of delayed hypersensitivity reactions by cinnamyl 1-thioglycosides

  摘要：

  Cinnamyl 1-thio-alpha-D-manno(and L-rhamno)pyranosides have good inhibitory effects in an antigen-specific T cell proliferation assay. The beta anomers are slightly less effective than the alpha anomers. The 6-substituted analogues of cinnamyl 1-thio-alpha-D-mannopyranoside such as 6-deoxy and 6-O-methyl derivatives also block macrophages in presenting the antigen to T cells. D-Mannose and L-rhamnose, when tested by themselves with no modifications, did not block at concentrations up to 1 mM. These cinnamyl 1-thioglycosides when given ip or po at 3-30 mg/kg to mice significantly inhibited the delayed type hypersensitivity reaction as measured by footpad swelling.

  DOI：

  10.1021/jm00387a021

文献信息

• US4554349A
  申请人：——

  公开号：US4554349A

  公开（公告）日：1985-11-19
• Inhibition of delayed hypersensitivity reactions by cinnamyl 1-thioglycosides
  作者：Mitree M. Ponpipom、Robert L. Bugianesi、Thomas J. Blake

  DOI：10.1021/jm00387a021

  日期：1987.4

  Cinnamyl 1-thio-alpha-D-manno(and L-rhamno)pyranosides have good inhibitory effects in an antigen-specific T cell proliferation assay. The beta anomers are slightly less effective than the alpha anomers. The 6-substituted analogues of cinnamyl 1-thio-alpha-D-mannopyranoside such as 6-deoxy and 6-O-methyl derivatives also block macrophages in presenting the antigen to T cells. D-Mannose and L-rhamnose, when tested by themselves with no modifications, did not block at concentrations up to 1 mM. These cinnamyl 1-thioglycosides when given ip or po at 3-30 mg/kg to mice significantly inhibited the delayed type hypersensitivity reaction as measured by footpad swelling.