(3aS,4S,6R,6aR)-6-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid | 219755-20-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (3aS,4S,6R,6aR)-6-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid
• 英文别名: 2',3'-O-isopropylidene-guanosine-5'-carboxylic acid；2'-3'-isopropylideneguanosine-5'-carboxylic acid；isopropylideneguanosine-5'carboxylic acid；1-(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)-1-deoxy-2,3-O-(1-methylethylidene)-I(2)-D-ribofuranuronic acid；(3aR,4R,6S,6aS)-4-(2-amino-6-oxo-1H-purin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxylic acid
• CAS: 219755-20-1
• 化学式: C₁₃H₁₅N₅O₆
• 分子量: 337.292
• InChiKey: AQTVKLMZWPWDEH-HEZDBXPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6R,6aR)-6-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 二碘甲烷 、 异丙烯基氯甲酸酯 、 四乙基氯化铵 、 碘 、 N,N-二甲基苯胺 、 三乙胺 、 三氯氧磷 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 DMF (N,N-dimethyl-formamide) 、 乙醇 、 乙腈 为溶剂， 反应 17.92h， 生成
  参考文献：
  名称：

  [EN] COMPOUNDS USEFUL AS A3 ADENOSINE RECEPTOR AGONISTS
  [FR] COMPOSES UTILES COMME AGONISTES DES RECEPTEURS DE L'ADENOSINE A3

  摘要：

  公开号：

  WO2005012323A3
• 作为产物：
  描述：

  2',3'-O-异丙亚基鸟苷 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 6.0h， 以62%的产率得到(3aS,4S,6R,6aR)-6-(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid
  参考文献：
  名称：

  超分子水凝胶释放生物活性挥发物：可逆酰基hydr的形成对凝胶稳定性和挥发性化合物蒸发的影响†

  摘要：

  在碱金属阳离子的存在下，鸟苷5'-酰肼（1）通过选择性自组装成G四元结构而形成稳定的超分子水凝胶。除了物理上被捕获在凝胶结构中之外，生物活性醛或酮还可以与G四元组外围的游离酰肼功能可逆地反应，形成酰基hydr。这种特殊性使得水凝胶作为缓慢释放生物活性羰基衍生物的递送系统而引起人们的兴趣。发现由1形成的水凝胶比从中获得的凝胶更稳定鸟苷。可以通过间接方法证明生物活性挥发物的物理包容和可逆的形成。通过振荡盘流变学测量来测量凝胶稳定性，这表明凝胶的热力学平衡是缓慢的，并且需要几个冷却和加热循环。此外，结合流变学数据和香料蒸发的动态顶空分析表明，某些羰基化合物的可逆形成影响挥发物的释放，而凝胶的绝对稳定性似乎对蒸发速率没有影响。

  DOI：

  10.1039/c0ob01139h

文献信息

• Design, synthesis and evaluation of N⁶-substituted 2-aminoadenosine-5′-N-methylcarboxamides as A₃ adenosine receptor agonists
  作者：Shane M. Devine、Lauren T. May、Peter J. Scammells

  DOI：10.1039/c3md00364g

  日期：——

  A series of N⁶-substituted 2-aminoadenosine-5′-N-methylcarboxamides were synthesized from the versatile intermediate, O⁶-(benzotriazol-1-yl)-2-amino-2′,3′-O-isopropylideneinosine-5′-N-methylcarboxamide (1) and evaluated as A₃ adenosine receptor agonists.

  一系列N6-取代2-氨基腺苷-5'-N-甲基羧酰胺从多功能中间体O6-(苯并三唑-1-基)-2-氨基-2',3'-O-异丙基葡萄糖苷-5'-N-甲基羧酰胺（1）合成，并作为A3腺苷受体激动剂进行评价。
• Synthesis and biological evaluation of novel neamine–nucleoside conjugates potentially targeting to RNAs
  作者：Yanli Xu、Hongwei Jin、Zhenjun Yang、Liangren Zhang、Lihe Zhang

  DOI：10.1016/j.tet.2009.04.084

  日期：2009.7

  Eighteen novel neamine-nucleoside conjugates with ethylenediamine-lysine or ethylenediamine-arginine as the linker were synthesized and their potential binding to A site of 16S RNA and TAR RNA was evaluated using SPR (surface plasmon resonance). Compared with neamine, compounds 10i and 10q show 6.3 and 4.8 times potential in binding to A site of 16S RNA and eight and six times potential in binding to TAR RNA, respectively. According to the data of SPR, it indicates that amino acid residue and nucleobase moieties of the designed neamine-nucleosides conjugates exhibit the important contributions for the binding to A site of 16S RNA and TAR RNA. The molecular docking Study on the interaction between the ligands and A site of 16S RNA is in agreement with the experimental data. The novel type of modification may provide a promising way for the development of neamine derivatives effectively targeting to RNAs. (C) 2009 Elsevier Ltd. All rights reserved.
• Enhancing the Mechanical Properties of Guanosine-Based Supramolecular Hydrogels with Guanosine-Containing Polymers
  作者：Amanda E. Way、Angie B. Korpusik、Taylor B. Dorsey、Lauren E. Buerkle、Horst A. von Recum、Stuart J. Rowan

  DOI：10.1021/ma402618z

  日期：2014.3.11

  We demonstrate that multivalent, polymeric 8-methoxyguanosine derivatives based on poly(dimethylacrylamide) can enhance the mechanical properties of the low molecular weight hydrogelator 8-methoxy-2',3',5'-tri-O-acetylguanosine at biologically relevant salt concentrations. It is proposed that these nongelling polymeric derivatives, under the conditions studied, can result in a significant enhancement of these supramolecular gels (e.g., for gels containing 1 wt % gelator G' can be increased from ca. 2000 Pa with no additive to 80 000 Pa) by acting as supramolecular cross-linking units. Two competing mechanisms appear to play a role in these cogels. At low polymer concentrations the guanosine-containing polymers tend to act more as solubilizing agents for the gelator, thus weakening the gels, while at high guanosine-containing polymer concentrations the gels show a marked enhancement in mechanical properties consistent with them acting as supramolecular cross-linking agents. As such, the thermomechanical properties of these cogels depend on both the polymer:low molecular weight gelator ratio and the number of 8-methoxyguanosine repeat units present in the polymer additive. Thus, these polymeric guanosine-based additives impart the ability to tailor both the modulus and shear sensitivity of the gels. For example, cogels with a modulus ranging between ca. 95 and 80 000 Pa can be obtained through judicious selection of the type and amount of polymer additive.
• Linear and convergent approaches to 2-substituted adenosine-5′-N-alkylcarboxamides
  作者：Richard C. Foitzik、Shane M. Devine、Nicholas E. Hausler、Peter J. Scammells

  DOI：10.1016/j.tet.2009.08.057

  日期：2009.10

  Herein we report both linear and convergent pathways for the preparation of 2-alkynyl substituted adenosine-5'-N-ethylcarboxamides via the versatile synthetic intermediate, 2-iodoadenosine-5'-N-ethylcarboxamide (13). The linear approach afforded 13 in an overall yield of 30% from guanosine over eight synthetic steps. The convergent approach was shorter, but proceeded in lower yield (five steps, 20% yield). Both approaches compare favourably with previously reported syntheses of 13, which has been prepared in 15% yield from guanosine over nine steps. 2-Iodoadenosine-5'-N-ethylcarboxamide (13) was subsequently converted to HENECA (2) and PHPNECA (3) to exemplify the utility of this approach for the preparation of potent A(2A) adenosine receptor agonists. The linear approach was also amenable to the synthesis of 2-fluoropurine ribosides, which were subsequently elaborated into 2-alkylaminoadenosine-5'-N-ethylcarboxamides. Furthermore, both of these synthetic approaches are readily amenable to the synthesis of adenosine analogues with varied 2-, 6- and 5'-substitution patterns. (c) 2009 Elsevier Ltd. All rights reserved.