5-O-ethyl-α/β-D-ribofuranose | 114405-60-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-ethyl-α/β-D-ribofuranose
• 英文别名: 5-O-ethyl-D-ribose；(3R,4S,5R)-5-(ethoxymethyl)oxolane-2,3,4-triol
• CAS: 114405-60-6；114405-61-7
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: CDGUERHFNFSFHZ-RKEPMNIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-ethyl-α/β-D-ribofuranose 在 吡啶 、 硫酸 、 sodium methylate 、 四氯化锡 、 magnesium sulfate 、 fluorine 、 calcium carbonate 作用下， 以 吡啶 、 甲醇 、 溶剂黄146 为溶剂， 反应 54.5h， 生成 5'-O-ethyl-5-fluorouridine
  参考文献：
  名称：

  Holy, Antonin; Koenig, Joachim; Vesely, Jiri, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 6, p. 1589 - 1608

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基-2,3-O-异亚丙基-D-呋喃核糖苷 在 硫酸 、 sodium hydride 作用下， 以 甲醇 、 水 为溶剂， 反应 23.5h， 生成 5-O-ethyl-α/β-D-ribofuranose
  参考文献：
  名称：

  Holy, Antonin; Koenig, Joachim; Vesely, Jiri, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 6, p. 1589 - 1608

  摘要：

  DOI：

文献信息

• C2,5'- disubstituted and N6, c2,5'- trisubstituted adenosine derivatives and their different uses
  申请人：——

  公开号：US20040132686A1

  公开（公告）日：2004-07-08

  The present invention concerns novel C2,5′-disubstituted and N 6 ′,C2,5′-trisubstituted adenosine derivatives and their different uses. These adenosine derivatives were found to be potent adenosine receptor agonists and thus are of a therapeutic value in the treatment and prophylaxis of diseases and disorders affected by adenosine receptor agonists.

  本发明涉及新型的C2,5'-二取代和N6',C2,5'-三取代腺苷衍生物及其不同的用途。发现这些腺苷衍生物是有效的腺苷受体激动剂，因此在治疗和预防受腺苷受体激动剂影响的疾病和障碍方面具有治疗价值。
• Synthesis and Antiviral Activity of Certain 5‘-Modified Analogs of 2,5,6-Trichloro-1-(β-<scp>d</scp>-ribofuranosyl)benzimidazole
  作者：Kristjan S. Gudmundsson、John C. Drach、Linda L. Wotring、Leroy B. Townsend

  DOI：10.1021/jm9604888

  日期：1997.2.1

  A series of 5'-modified 2,5,6-trichlorobenzimidazole ribonucleosides has been synthesized and tested for activity against two human herpesviruses and for cytotoxicity. The 5'-methoxy, 5'-ethoxy, and 5'-butoxy analogs of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) were prepared by coupling the appropriate 5-O-alkyl-1,2,3-tri-O-acetyl-beta-D-ribose derivatives with 2,5,6-trichlorobenzimidazole followed by removal of the protecting groups. The 5'-deoxy-5'-fluoro, -5'-chloro, -5'-bromo, -5'-iodo, -5'-azido, and -5'-thiomethyl derivatives were synthesized in a similar fashion. All of these 5'-modified derivatives had significant activity against HCMV in plaque and yield reduction assays (IC50's = 0.5-14.2 mu M) but had little activity (IC50's > 100 mu M) against HSV-1. This pattern is similar to the antiviral activity profile observed for TCRB. The 5'-halogenated derivatives were more active than the other 5'-modified derivatives with antiviral activity well separated from cytotoxicity. In general, cytotoxicity of all the 5'-modified derivatives was greater in human foreskin fibroblasts (HFF cells) than in L1210 or K-B tumor cells. These results indicate that the viral target tolerates significant modifications of TCRB at the 5'-position without adversely affecting activity against HCMV, whereas the 5'-modifications increased cytotoxicity in human diploid cells.
• 5‘-<i>O</i>-Alkyl Ethers of<i> N</i>,2-Substituted Adenosine Derivatives:  Partial Agonists for the Adenosine A₁ and A₃ Receptors
  作者：Erica W. van Tilburg、Pieter A. M. van der Klein、Jacobien von Frijtag Drabbe Künzel、Miriam de Groote、Christina Stannek、Anna Lorenzen、Ad P. IJzerman

  DOI：10.1021/jm001114o

  日期：2001.8.1

  New N,5'-di- and N,2,5'-trisubstituted adenosine derivatives were synthesized in good overall yields. Appropriate 5-O-alkyl-substituted ribose moieties were coupled to 6-chloropurine or 2,6-dichloropurine via Vorbruggen's glycosylation method. Subsequent amination and deprotection of the intermediates yielded compounds 18-35. Binding affinities were determined for rat adenosine A(1) and A(2A) receptors and the human A(3) receptor. The ability of compounds 18-35 to inhibit forskolin-induced (10 muM) cyclic AMP (cAMP) production and their ability to stimulate guanosine 5'-O-(3-[S-35]thio)triphosphate ([S-35]GTP gammaS) binding, via either the adenosine A(1) receptor or the adenosine A(3) receptor, were assessed. N-Cyclopentyl-substituted adenosine derivatives displayed affinities in the low nanomolar range for the adenosine A(1) receptor, whereas N-(3-iodobenzyl)-substituted derivatives had high affinity for the adenosine A(3) receptor. Compound 22 had the highest affinity for the adenosine A(3) receptor (K-i value of 16 nM), and compounds 20 and 26 had the highest affinities for the adenosine A(3) receptor (K-i values of 4 and 3 nM, respectively). A chlorine substituent at the 2-position either did not affect or slightly increased the adenosine A(3) receptor affinity, whereas the A(3) receptor affinity was affected differently, depending on the N-substituent. Furthermore, the introduction of chlorine slightly increased the A(3)/A(1) selectivity ratio. At the 5 ' -position, an O-methyl substituent induced the highest adenosine A(1) receptor affinity, whereas an O-ethyl substituent did so for the A(3) receptor. All compounds showed partial agonistic effects in both the cAMP and [S-35]GTP gammaS assays, although more marked in the latter assay. In general, the 2-chloro derivatives seemed to have lower intrinsic activities compared to the 2-H-substituted compounds on both the adenosine A(1) and the adenosine A(3) receptors. The compounds with an N-(3-iodobenzyl) substituent displayed the lowest intrinsic activities. Finally, all compounds also showed partially antagonistic behavior in the [S-35]GTP gammaS assay.
• US7084127B2
  申请人：——

  公开号：US7084127B2

  公开（公告）日：2006-08-01
• Holy, Antonin; Koenig, Joachim; Vesely, Jiri, Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 6, p. 1589 - 1608
  作者：Holy, Antonin、Koenig, Joachim、Vesely, Jiri、Cech, Dieter、Votruba, Ivan、Clercq, Erik de

  DOI：——

  日期：——