cinnamyl 6-O-methyl-1-thio-β-D-mannopyranoside | 101648-47-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cinnamyl 6-O-methyl-1-thio-β-D-mannopyranoside
• 英文别名: cinnamyl 6-O-methyl-1-thio-α-D-mannopyranoside；(2R,3S,4S,5S,6R)-2-(methoxymethyl)-6-[(E)-3-phenylprop-2-enyl]sulfanyloxane-3,4,5-triol
• CAS: 101648-47-9
• 化学式: C₁₆H₂₂O₅S
• 分子量: 326.414
• InChiKey: XNYIFEDOLJRROM-SRLXZSMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  cinnamyl 2,3,4-tri-O-acetyl-6-O-methyl-1-thio-β-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 cinnamyl 6-O-methyl-1-thio-β-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.