(2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-carboxylic acid amide | 391871-61-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-carboxylic acid amide
• 英文别名: (2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolane-2-carboxamide
• CAS: 391871-61-7
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: LUOWZDBIUCNQSS-TXICZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  劳森试剂 、 (2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-carboxylic acid amide 、 1,4-二氧六环 在 ice water 、 SiO2 、 graded eluent 、 ethyl acetate n-hexane 作用下， 反应 64.0h， 以to give the title compound as a pale cream solid (3.32 g, 68%)的产率得到(2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-carbothioic Acid Amide Tribenzoate
  参考文献：
  名称：

  Non-natural carbon-linked nucleotides and dinucleotides

  摘要：

  本文描述了式（1）的核苷酸衍生物，其中：G是氢原子或可选取代的脂肪族，杂脂族，环脂族，多环脂族，芳香族或杂芳香族基团或非天然的碳链核苷酸，如本文所定义；G'是本文所定义的非天然碳链核苷酸；n为零或整数1或2；m为零或整数1或2；以及其盐，溶剂合物，水合物和N-氧化物。这些化合物是P2Y受体激动剂，可用于预防和治疗涉及异常分泌机制的疾病和障碍，例如粘液纤毛清除机制的功能不足或泪液分泌异常，或用于治疗涉及不适当细胞葡萄糖摄取的疾病。

  公开号：

  US20050009777A1
• 作为产物：
  描述：

  2,3,5-tri-O-benzoyl-β-D-ribofuranosyl-1-carbonitrile 在 氨 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以34%的产率得到(2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydrofuran-2-carboxylic acid amide
  参考文献：
  名称：

  Synthesis and biochemical evaluation of guanidino-alkyl-ribitol derivatives as nucleoside hydrolase inhibitors

  摘要：

  Nucleoside hydrolase (NH) is a key enzyme in the purine salvage pathway. The purine specificity of the IAG-NH from Trypanosoma vivax is at least in part due to cation-pi-stacking interactions. Guanidinium ions can be involved in cation-pi-stacking interactions, therefore a series of guanidino-alkyl-ribitol derivatives were synthesized in order to examine the binding affinity of these compounds towards the target enzyme. The compounds show moderate to good inhibiting activity towards the IAG-NH from T. vivax. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.027

文献信息

• NON-NATURAL CARBON-LINKED NUCLEOTIDES AND DINUCLEOTIDES
  申请人：Celltech R & D Limited

  公开号：EP1409503A1

  公开（公告）日：2004-04-21
• [EN] NON-NATURAL CARBON-LINKED NUCLEOTIDES AND DINUCLEOTIDES<br/>[FR] NUCLEOTIDES ET DINUCLEOTIDES A LIAISON CARBONE NON NATURELS
  申请人：CELLTECH R&D LTD

  公开号：WO2003011885A1

  公开（公告）日：2003-02-13

  Nucleotide derivatives of formula (1) are described, wherein: G is a hydrogen atom or an optionally substituted aliphatic, heteroaliphatic, cycloaliphatic, polycycloaliphatic, aromatic or heteroaromatic group or a non natural carbon-linked nucleoside as defined herein; G' is a non-natural carbon-linked nucleoside as defined herein; n is zero, or the integer 1 or 2; m is zero or the integer 1 or 2; and the salts, solvates, hydrates and N-oxides thereof. The compounds are P2Y receptor agonists and are of use in the prophylaxis and treatment of diseases and disorders involving abnormal secretory mechanisms such as inadequate functioning of mucociliary clearance mechanisms or abnormal tear secretion or in the treatment of diseases involving inappropriate cellular glucose uptake.
• Synthesis and biochemical evaluation of guanidino-alkyl-ribitol derivatives as nucleoside hydrolase inhibitors
  作者：A. Goeminne、M. McNaughton、G. Bal、G. Surpateanu、P. Van Der Veken、S. De Prol、W. Versées、J. Steyaert、A. Haemers、K. Augustyns

  DOI：10.1016/j.ejmech.2007.03.027

  日期：2008.2

  Nucleoside hydrolase (NH) is a key enzyme in the purine salvage pathway. The purine specificity of the IAG-NH from Trypanosoma vivax is at least in part due to cation-pi-stacking interactions. Guanidinium ions can be involved in cation-pi-stacking interactions, therefore a series of guanidino-alkyl-ribitol derivatives were synthesized in order to examine the binding affinity of these compounds towards the target enzyme. The compounds show moderate to good inhibiting activity towards the IAG-NH from T. vivax. (c) 2007 Elsevier Masson SAS. All rights reserved.
• Non-natural carbon-linked nucleotides and dinucleotides
  申请人：Mack Robert Stephen

  公开号：US20050009777A1

  公开（公告）日：2005-01-13

  Nucleotide derivatives of formula (1) are described, wherein: G is a hydrogen atom or an optionally substituted aliphatic, heteroaliphatic, cycloaliphatic, polycycloaliphatic, aromatic or heteroaromatic group or a non natural carbon-linked nucleoside as defined herein; G′ is a non-natural carbon-linked nucleoside as defined herein; n is zero, or the integer 1 or 2; m is zero or the integer 1 or 2; and the salts, solvates, hydrates and N-oxides thereof. The compounds are P2Y receptor agonists and are of use in the prophylaxis and treatment of diseases and disorders involving abnormal secretory mechanisms such as inadequate functioning of mucociliary clearance mechanisms or abnormal tear secretion or in the treatment of diseases involving inappropriate cellular glucose uptake.

  本文描述了式（1）的核苷酸衍生物，其中：G是氢原子或可选取代的脂肪族，杂脂族，环脂族，多环脂族，芳香族或杂芳香族基团或非天然的碳链核苷酸，如本文所定义；G'是本文所定义的非天然碳链核苷酸；n为零或整数1或2；m为零或整数1或2；以及其盐，溶剂合物，水合物和N-氧化物。这些化合物是P2Y受体激动剂，可用于预防和治疗涉及异常分泌机制的疾病和障碍，例如粘液纤毛清除机制的功能不足或泪液分泌异常，或用于治疗涉及不适当细胞葡萄糖摄取的疾病。