5-β-D-ribofuranosylfuran-3-carboxylic acid | 307311-21-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-β-D-ribofuranosylfuran-3-carboxylic acid
• 英文别名: 5-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]furan-3-carboxylic acid
• CAS: 307311-21-3
• 化学式: C₁₀H₁₂O₇
• 分子量: 244.201
• InChiKey: LTEFONVBUXHMOA-BGZDPUMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  120
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  右旋苯丙胺 、 5-β-D-ribofuranosylfuran-3-carboxylic acid 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以70%的产率得到(2'R,3'R,4'S,5'R)-3',4'-Dihydroxy-5'-hydroxymethyl-2',3',4',5'-tetrahydro-[2,2']bifuranyl-4-carboxylic acid ((S)-1-methyl-2-phenyl-ethyl)-amide
  参考文献：
  名称：

  c-nucleoside analogues of furanfurin as ligands to a1 adenosine receptors

  摘要：

  Furanfurin (2-beta-D-ribofuranosylfuran-4-carboxamide) derivatives and analogues were synthesized and their affinity for adenosine receptors was determined. The agonistic behavior of furanfurin against A(1) receptors is preserved only when the furan ring is substituted with isosteric pentatomic ring systems such as oxazole, thiazole or thiophene, and the carboxamide group is unsubstituted. Replacement of the hydrogen atoms of the carboxamide group with alkyl, cycloalkyl or arylalkyl groups generates compounds endowed with moderate antagonistic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00167-x
• 作为产物：
  描述：

  ethyl 5-β-D-ribofuranosylfuran-3-carboxylate 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 以78%的产率得到5-β-D-ribofuranosylfuran-3-carboxylic acid
  参考文献：
  名称：

  c-nucleoside analogues of furanfurin as ligands to a1 adenosine receptors

  摘要：

  Furanfurin (2-beta-D-ribofuranosylfuran-4-carboxamide) derivatives and analogues were synthesized and their affinity for adenosine receptors was determined. The agonistic behavior of furanfurin against A(1) receptors is preserved only when the furan ring is substituted with isosteric pentatomic ring systems such as oxazole, thiazole or thiophene, and the carboxamide group is unsubstituted. Replacement of the hydrogen atoms of the carboxamide group with alkyl, cycloalkyl or arylalkyl groups generates compounds endowed with moderate antagonistic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00167-x

文献信息

• c-nucleoside analogues of furanfurin as ligands to a1 adenosine receptors
  作者：Palmarisa Franchetti、Loredana Cappellacci、Stefano Marchetti、Claudia Martini、Barbara Costa、Katia Varani、Pier Andrea Borea、Mario Grifantini

  DOI：10.1016/s0968-0896(00)00167-x

  日期：2000.9

  Furanfurin (2-beta-D-ribofuranosylfuran-4-carboxamide) derivatives and analogues were synthesized and their affinity for adenosine receptors was determined. The agonistic behavior of furanfurin against A(1) receptors is preserved only when the furan ring is substituted with isosteric pentatomic ring systems such as oxazole, thiazole or thiophene, and the carboxamide group is unsubstituted. Replacement of the hydrogen atoms of the carboxamide group with alkyl, cycloalkyl or arylalkyl groups generates compounds endowed with moderate antagonistic activity. (C) 2000 Elsevier Science Ltd. All rights reserved.