ethyl 5-β-D-ribofuranosylfuran-3-carboxylate | 169823-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 5-β-D-ribofuranosylfuran-3-carboxylate
• 英文别名: ethyl 5-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]furan-3-carboxylate
• CAS: 169823-62-5
• 化学式: C₁₂H₁₆O₇
• 分子量: 272.255
• InChiKey: MPIDAWCFBJLXSK-DBIOUOCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5-β-D-ribofuranosylfuran-3-carboxylate 在 sodium hydroxide 、 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 、 水 为溶剂， 反应 4.5h， 生成 (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：

  四乙酰核糖 在 sodium ethanolate 、 四氯化锡 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 19.0h， 生成 ethyl 5-β-D-ribofuranosylfuran-3-carboxylate
  参考文献：
  名称：

  呋喃呋喃和噻吩呋喃：两种新型的噻唑啉类似物。合成，结构，抗肿瘤活性以及与肌苷单磷酸脱氢酶的相互作用。

  摘要：

  描述了噻唑呋喃的呋喃和噻吩类似物（分别为呋喃呋喃和噻吩呋喃）的合成。用1,2,3,5-四-O-乙酰基-D-呋喃呋喃糖将三呋喃甲酸乙酯（6）或3-噻吩甲酸乙酯（18）直接用氯化锡催化的C-糖基化反应得到2-和5-糖基化的区域异构体，是α和β异头异构体的混合物，以及β-2,5-二糖基化衍生物。5-（2,3,5-三-O-乙酰基-β-D-呋喃呋喃糖基）呋喃-3-羧酸酯（9 beta）和5-（2,3,5-三-O-乙酰基-乙基-乙基的脱保护β-D-呋喃呋喃糖基）噻吩-3-羧酸盐（20 beta）与乙醇钠制得5-β-D-呋喃呋喃糖基呋喃-3-羧酸乙酯（12 beta）和5-β-D-呋喃呋喃糖基噻吩-3-羧酸乙酯（23 β）转化为5-β-D-呋喃呋喃糖基呋喃-3-羧酰胺（呋喃呋喃，4）和5-β-D-呋喃呋喃糖基噻吩-3-甲酰胺（thiophenfurin，5）与氢氧化铵反应。通过1 H-NMR和质子-质子

  DOI：

  10.1021/jm00019a013

文献信息

• Synthesis, Antitumor Activity and Crystallographic Studies of Analogues of Tiazofurin
  作者：L. Cappellacci、P. Franchetti、M. Grifantini、L. Messini、G. Abu Sheikha、G. Nocentini、R. Moraca、B. M. Goldstein

  DOI：10.1080/15257779508012440

  日期：1995.5.1

  The syntheses and antitumor activity of 2-beta-D-ribofuranosylfuran-4-carboxamide (furanfurin) and 2-beta-D-ribofuranosylthiophene-4-carboxamide (thiophenfurin) are reported. The X-ray structure of ethyl 2-beta-D-ribofuranosylthiophene-4-carboxylate, precursor of thiophenfurin, is also presented. Only thiophenfurin showed activity as an antitumor agent both in vitro and in vivo.
• 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.
• Furanfurin and Thiophenfurin: Two Novel Tiazofurin Analogs. Synthesis, Structure, Antitumor Activity, and Interactions with Inosine Monophosphate Dehydrogenase
  作者：Palmarisa Franchetti、Loredana Cappellacci、Mario Grifantini、Anna Barzi、Giuseppe Nocentini、Hongyoan Yang、Ayrn O'Connor、Hiremagalur N. Jayaram、Christopher Carrell、Barry M. Goldstein

  DOI：10.1021/jm00019a013

  日期：1995.9

  5-tetra-O-acetyl-D-ribofuranose gave 2- and 5-glycosylated regioisomers, as a mixture of alpha- and beta-anomers, and the beta-2,5-diglycosylated derivatives. Deprotection of ethyl 5-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)furan-3-carboxylate (9 beta) and ethyl 5-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)thiophene-3-carboxylate (20 beta) with sodium ethoxide afforded ethyl 5-beta-D-ribofuranosylfuran-3-carboxylate

  描述了噻唑呋喃的呋喃和噻吩类似物（分别为呋喃呋喃和噻吩呋喃）的合成。用1,2,3,5-四-O-乙酰基-D-呋喃呋喃糖将三呋喃甲酸乙酯（6）或3-噻吩甲酸乙酯（18）直接用氯化锡催化的C-糖基化反应得到2-和5-糖基化的区域异构体，是α和β异头异构体的混合物，以及β-2,5-二糖基化衍生物。5-（2,3,5-三-O-乙酰基-β-D-呋喃呋喃糖基）呋喃-3-羧酸酯（9 beta）和5-（2,3,5-三-O-乙酰基-乙基-乙基的脱保护β-D-呋喃呋喃糖基）噻吩-3-羧酸盐（20 beta）与乙醇钠制得5-β-D-呋喃呋喃糖基呋喃-3-羧酸乙酯（12 beta）和5-β-D-呋喃呋喃糖基噻吩-3-羧酸乙酯（23 β）转化为5-β-D-呋喃呋喃糖基呋喃-3-羧酰胺（呋喃呋喃，4）和5-β-D-呋喃呋喃糖基噻吩-3-甲酰胺（thiophenfurin，5）与氢氧化铵反应。通过1 H-NMR和质子-质子