1-氨基-1-脱氧-D-果糖乙酸盐 | 1201794-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-氨基-1-脱氧-D-果糖乙酸盐
• 英文名称: 1-amino-1-deoxy-D-fructose acetate
• 英文别名: 1-amino-1-deoxy-D-fructose acetic acid salt；fructosamine acetate；fructosamine acetic acid salt；(3S,4S,5R)-2-(aminomethyl)-5-(hydroxymethyl)tetrahydrofuran-2,3,4-triol acetate；acetic acid;(3S,4S,5R)-2-(aminomethyl)-5-(hydroxymethyl)oxolane-2,3,4-triol
• CAS: 1201794-87-7
• 化学式: C₂H₄O₂*C₆H₁₃NO₅
• 分子量: 239.225
• InChiKey: XIHYWBCNHWTTOI-WYVTXLGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.16
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  153.47
• 氢给体数：
  6.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,2-二氟-2-苯乙腈 、 1-氨基-1-脱氧-D-果糖乙酸盐 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以34%的产率得到phenyl(4-((1R,2S,3R)-1,2,3,4-tetrahydroxybutyl)-1H-imidazol-2-yl)methanone
  参考文献：
  名称：

  Inhibition of Sphingosine-1-Phosphate Lyase for the Treatment of Autoimmune Disorders

  摘要：

  During nearly a decade of research dedicated to the study of sphingosine signaling pathways, we identified sphingosine-1-phosphate lyase (S1PL) as a drug target for the treatment of autoimmune disorders. S1PL catalyzes the irreversible decomposition of sphingosine-1-phosphate (S1P) by a retro-aldol fragmentation that yields hexadecanaldehyde and phosphoethanolamine. Genetic models demonstrated that mice expressing reduced S1PL activity had decreased numbers of circulating lymphocytes due to altered lymphocyte trafficking, which prevented disease development in multiple models of autoimmune disease. Mechanistic studies of lymphoid tissue following oral administration of 2-acetyl-4(5)-(1(R),2(S),3(R),4-tetrahydroxybutyl)-imidazole (THI) 3 showed a clear relationship between reduced lyase activity, elevated S I P levels, and lower levels of circulating lymphocytes. Our internal medicinal chemistry efforts discovered potent analogues of 3 bearing heterocycles as chemical equivalents of the pendant carbonyl present in the parent structure. Reduction of S1PL activity by oral administration of these analogues recapitulated the phenotype of mice with genetically reduced S1PL expression.

  DOI：

  10.1021/jm900278w
• 作为产物：
  描述：

  D-葡萄糖 、 溶剂黄146 在 二苄胺 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 水 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以85%的产率得到1-氨基-1-脱氧-D-果糖乙酸盐
  参考文献：
  名称：

  Inhibition of Sphingosine-1-Phosphate Lyase for the Treatment of Autoimmune Disorders

  摘要：

  During nearly a decade of research dedicated to the study of sphingosine signaling pathways, we identified sphingosine-1-phosphate lyase (S1PL) as a drug target for the treatment of autoimmune disorders. S1PL catalyzes the irreversible decomposition of sphingosine-1-phosphate (S1P) by a retro-aldol fragmentation that yields hexadecanaldehyde and phosphoethanolamine. Genetic models demonstrated that mice expressing reduced S1PL activity had decreased numbers of circulating lymphocytes due to altered lymphocyte trafficking, which prevented disease development in multiple models of autoimmune disease. Mechanistic studies of lymphoid tissue following oral administration of 2-acetyl-4(5)-(1(R),2(S),3(R),4-tetrahydroxybutyl)-imidazole (THI) 3 showed a clear relationship between reduced lyase activity, elevated S I P levels, and lower levels of circulating lymphocytes. Our internal medicinal chemistry efforts discovered potent analogues of 3 bearing heterocycles as chemical equivalents of the pendant carbonyl present in the parent structure. Reduction of S1PL activity by oral administration of these analogues recapitulated the phenotype of mice with genetically reduced S1PL expression.

  DOI：

  10.1021/jm900278w

文献信息

• METHODS OF PREPARING IMIDAZOLE-BASED BICYCLIC COMPOUNDS
  申请人：Guohua Jason

  公开号：US20090318705A1

  公开（公告）日：2009-12-24

  Methods of preparing compounds of formula I are disclosed:

  公开了制备式I化合物的方法：
• SOLID FORMS OF (1R,2S,3R)-1-(2-(ISOXAZOL-3-YL)-1H-IMIDAZOL-4-YL)BUTANE-1,2,3,4-TETRAOL AND METHODS OF THEIR USE
  申请人：Burgoon Hugh Alfred

  公开号：US20090318516A1

  公开（公告）日：2009-12-24

  Solid forms of (1R,2S,3R)-1-(2-(isoxazol-3-yl)-1H-imidazol-4-yl)butane-1,2,3,4-tetraol and hydrates thereof are disclosed, as well as compositions comprising them and methods of their use.

  固体形式的(1R,2S,3R)-1-(2-(异噁唑-3-基)-1H-咪唑-4-基)丁烷-1,2,3,4-四醇及其水合物被披露，以及包含它们的组合物和使用方法。
• A Phosphorescent Rhenium(I) Tricarbonyl Polypyridine Complex Appended with a Fructose Pendant That Exhibits Photocytotoxicity and Enhanced Uptake by Breast Cancer Cells
  作者：Kenneth Yin Zhang、Karson Ka-Shun Tso、Man-Wai Louie、Hua-Wei Liu、Kenneth Kam-Wing Lo

  DOI：10.1021/om400612f

  日期：2013.9.23

  We demonstrated that the cytotoxicity of a phosphorescent rhenium(I) polypyridine complex with a fructose pendant was enhanced upon irradiation and the cellular uptake of the complex was mediated by fructose transporters and inhibited by unmodified fructose but was independent of glucose-specific transporters. This complex has been used to image breast cancer cells, where fructose transporters are

  我们证明，辐射后果糖侧基的磷光rh（I）聚吡啶复合物的细胞毒性得到增强，果糖转运蛋白介导了复合物的细胞摄取并被未修饰的果糖抑制，但与葡萄糖特异性转运蛋白无关。该复合物已用于对果糖转运蛋白过表达的乳腺癌细胞进行成像。
• A convenient synthesis of 2-acetyl-4(5)-(1R,2S,3R,4-tetrahydroxybutyl)imidazole
  作者：Kim M. Halweg、George Buchi

  DOI：10.1021/jo00207a049

  日期：1985.4
• WO2008/109314
  申请人：——

  公开号：——

  公开（公告）日：——