cinnamyl 6-amino-6-deoxy-1-thio-α-D-mannopyranoside | 101648-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cinnamyl 6-amino-6-deoxy-1-thio-α-D-mannopyranoside
• 英文别名: (2R,3S,4S,5S,6R)-2-(aminomethyl)-6-[(E)-3-phenylprop-2-enyl]sulfanyloxane-3,4,5-triol
• CAS: 101648-41-3
• 化学式: C₁₅H₂₁NO₄S
• 分子量: 311.402
• InChiKey: BZJDAYMZFAXIJR-OTTBBPIQSA-N

物化性质

• 沸点：
  554.8±50.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 cinnamyl 6-amino-6-deoxy-1-thio-α-D-mannopyranoside 以 甲醇 为溶剂， 以48%的产率得到cinnamyl 6-butyramido-6-deoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Aralkyl and aralkenyl glycosides as inhibitors of antigen-specific

  摘要：

  本发明涉及新颖的1-去氧糖苷，优选为1-去氧-D-甘露聚糖和1-去氧-L-鼠李糖苷，在吡喃糖环的1位具有芳基硫醚/芳基烯硫醚、芳基氧/芳基烯氧或芳基酰氨基/芳基烯酰氨基取代基；以及用于制备这些1-取代-1-去氧糖苷的新工艺，从相应的四-O-乙酰基糖吡喃糖溴化物或胺开始。1-取代-1-去氧糖苷的6-羟基也可以被其他功能基团取代。这些芳基硫醚/芳基烯硫醚、芳基氧/芳基烯氧和芳基酰氨基/芳基烯酰氨基1-去氧糖苷是抗原特异性T细胞增殖的有效抑制剂，也可用作延迟型超敏反应的抑制剂。

  公开号：

  US04554349A1
• 作为产物：
  描述：

  2-S-(2,3,4-tri-O-acetyl-6-O-(methylsulfonyl)-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide 在 potassium disulphite 、 sodium azide 、 硫化氢 、 sodium methylate 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 45.5h， 生成 cinnamyl 6-amino-6-deoxy-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

• Aralkyl and aralkenyl glycosides as inhibitors of antigen-specific
  申请人：Merck & Co., Inc.

  公开号：US04554349A1

  公开（公告）日：1985-11-19

  The invention disclosed herein relates to novel 1-deoxyglycosides, preferably 1-deoxy-D-mannopyranosides and 1-deoxy-L-rhamnopyranosides, having in the 1-position of the pyranose ring an aralkylthio/aralkenylthio, aralkyloxy/aralkenyloxy or aralkanoylamino/aralkenoylamino substituent; and to novel processes for preparing these 1-substituted-1-deoxyglycosides starting with the corresponding tetra-O-acetylglycopyranosyl bromide or amine. The 6-hydroxy group of 1-substituted-1 deoxyglycopyranosides can also be replaced by other functional groups. These aralkylthio/aralkenylthio, aralkyloxy/aralkenyloxy and aralkanoylamino/aralkenoylamino 1-deoxyglycosides are potent inhibitors of antigen-specific T-cell proliferation and are also useful as inhibitors of delayed-type hypersensitivity reactions.

  本发明涉及新颖的1-去氧糖苷，优选为1-去氧-D-甘露聚糖和1-去氧-L-鼠李糖苷，在吡喃糖环的1位具有芳基硫醚/芳基烯硫醚、芳基氧/芳基烯氧或芳基酰氨基/芳基烯酰氨基取代基；以及用于制备这些1-取代-1-去氧糖苷的新工艺，从相应的四-O-乙酰基糖吡喃糖溴化物或胺开始。1-取代-1-去氧糖苷的6-羟基也可以被其他功能基团取代。这些芳基硫醚/芳基烯硫醚、芳基氧/芳基烯氧和芳基酰氨基/芳基烯酰氨基1-去氧糖苷是抗原特异性T细胞增殖的有效抑制剂，也可用作延迟型超敏反应的抑制剂。
• 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.