2,4-diamino-N7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine | 120595-76-8

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 2,4-diamino-N7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
• 英文别名: (2R,3R,4S,5R)-2-(2,4-diaminopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 120595-76-8
• 化学式: C₁₁H₁₅N₅O₄
• 分子量: 281.271
• InChiKey: KBBXIXQBRHFCHC-DAGMQNCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  153
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,4-diamino-N7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 生成 7-(β-D-ribofuranosyl)-7H-pyrrolo<2,3-d>pyrimidin-2-amine
  参考文献：
  名称：

  SEELA, F.;ROSEMEYER, H.;BIESEWIG, A.;JURGENS, T., NUCLEOSIDES AND NUCLEOTIDES, 7,(1988) N-6, C. 581-584

  摘要：

  DOI：
• 作为产物：
  描述：

  2-amino-4-chloro-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 ammonium hydroxide 作用下， 反应 20.0h， 以82%的产率得到2,4-diamino-N7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  与7-去氮鸟苷相关的2,4-二取代的吡咯并[2,3- d ]嘧啶α-D-和β-D-呋喃核糖苷

  摘要：

  吡咯并[2,3- d ]嘧啶4a - d与5- O -[（1， 1-二甲基乙基）二甲基甲硅烷基] -2,3 - O-（1-甲基亚乙基）-α-D-核呋喃呋喃糖酰氯（5）立体选择得到保护的β-D-核苷6a - d（方案1）。相反，除少量的β-D-异头物外，β-D-卤代糖8产生相应的α-D-核苷（9a和9b）。去保护的核苷10a和11a被转化为4-取代的2-氨基吡咯并[2,3- d ]-嘧啶β-D-呋喃呋喃糖苷1。图10C，12，14，和16和到他们的α-d端基异构体，分别为（方案2）。从4b与5的反应中，分离出包含两个核碱基部分的糖基化产物7。

  DOI：

  10.1002/hlca.19900730710

文献信息

• A facile and improved synthesis of tubercidin and certain related pyrrolo[2,3-<i>d</i>]pyrimidine nucleosides by the stereospecific sodium salt glycosylation procedure
  作者：Kandasamy Ramasamy、Nobutaka Imamura、Roland K. Robins、Ganapathi R. Revankar

  DOI：10.1002/jhet.5570250652

  日期：1988.11

  simple synthesis of tubercidin (1), 7-deazaguanosine (2) and 2′-deoxy-7-deazaguanosine (14) has been accomplished using the sodium salt glycosylation procedure. Reaction of the sodium salt of 4-chloro- and 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine, 3 and 4, respectively, with 1-chloro-2,3-0-isopropylidene-5-0-(t-butyl)dimethylsilyl-α-D-ribofuranose (5) gave the corresponding protected nucleosides 6n and

  使用钠盐糖基化方法已经完成了结核菌素（1），7-脱氮鸟苷（2）和2'-脱氧-7-脱氮鸟苷（14）的简单合成。4-氯-和2-氨基-4-氯-吡咯并[2,3- d ]嘧啶的钠盐分别为3和4与1-氯-2,3- 0-异亚丙基-5-的反应0-（叔丁基）二甲基甲硅烷基-α-D-呋喃呋喃糖（5）给出了具有β-端基异构构型的相应的受保护核苷6n和7。取消保护6个提供的8，其在与甲醇氨一起加热后以优异的产率得到了结核菌素（1）。官能团7的转化，然后进行异异丙基化，得到2-氨基tubercidin（10）和2-氨基-7-β-D-呋喃呋喃糖基吡咯并[2,3- d ]嘧啶-4（3 H）-硫酮（11）。用1 N甲醇钠处理7，然后将其暴露于三氟乙酸水溶液中，并进行醚裂解，得到7-脱氮鸟苷（2）。还通过使用类似的反应顺序（采用4）制备了2'-Deoxy-7-deazaguanosine（14）和2'-deoxy-7-de
• Nucleobase-Functionalized 7-Deazaisoguanine and 7-Deazapurin-2,6-diamine Nucleosides: Halogenation, Cross-Coupling, and Cycloaddition
  作者：Zhenqiang Xia、Dasharath Kondhare、Somnath Shivaji Chandankar、Sachin A. Ingale、Peter Leonard、Frank Seela

  DOI：10.1021/acs.joc.3c02514

  日期：2024.2.2

  quantum yields) of azide–alkyne click adducts bearing pyrene as sensor groups were determined. Pyrene fluorescence was solvent-dependent and changed according to the linker lengths. Excimer emission was observed in dioxane for the long linker adduct. Bioorthogonal inverse-electron-demanding Diels–Alder cycloadditions (iEDDA) were conducted on the electron-rich vinyl groups of 7-deazaisoguanine and 7-deazapurin-2

  7-脱氮杂异鸟嘌呤和 7-脱氮杂嘌呤-2,6-二胺核糖核糖核糖核糖核苷和 2'-脱氧核糖核苷的 7 位通过卤素原子（氯、溴、碘）以及可点击的炔基和乙烯基侧链进行铜催化和描述了无铜环加成。在丙酮的作用下，解决了 7-碘化异鸟嘌呤核糖核苷和 2'-脱氧核糖核苷合成过程中出现的问题。研究了侧链和卤素原子对核苷 p K a值和疏水性的影响。卤代取代基按 Cl < Br < I 的顺序增加核苷的亲脂性，并降低质子化的 p K值。测定了带有芘作为传感器基团的叠氮-炔点击加合物的光物理性质（荧光、溶剂化显色和量子产率）。芘荧光依赖于溶剂并根据接头长度而变化。在二恶烷中观察到长连接子加合物的准分子发射。对作为亲二烯体的 7-deazaisoguanine 和 7-deazapurin-2,6-diamine 核苷的富电子乙烯基和 3,6-dipyridyl-1,2 进行生物正交逆电子需求 Diels-Alder
• Fluorine Substituted Adenosines As Probes of Nucleobase Protonation in Functional RNAs
  作者：Ian T. Suydam、Scott A. Strobel

  DOI：10.1021/ja803336y

  日期：2008.10.15

  Ionized nucleobases are required for folding, conformational switching, or catalysis in a number of functional RNAs. A common strategy to study these sites employs nucleoside analogues with perturbed pK(a), but the interpretation of these studies is often complicated by the chemical modification introduced, in particular modifications that add, remove, or translocate hydrogen bonding groups in addition to perturbing pKa values. In the present study we present a series of fluorine substituted adenosine analogues that produce large changes in N1 pK(a) values with minimal structural perturbation. These analogues include fluorine for hydrogen substitutions in the adenine ring of adenosine and 7-deaza-adenosine with resulting N1 pK(a) values spanning more than 4 pKa units. To demonstrate the utility of these analogues we have conducted a nucleotide analogue interference mapping (NAIM) study on a self-ligating construct of the Varkud Satellite (VS) ribozyme. We find that each of the analogues is readily incorporated by T7 RNA polymerase and produces fully active transcripts when substituted at the majority of sites. Strong interferences are observed for three sites known to be critical for VS ribozyme function, most notably A756. Substitutions at A756 lead to slight enhancements in activity for elevated pK(a) analogues and dramatic interferences in activity for reduced pK(a) analogues, supporting the proposed catalytic role for this base. The structural similarity of these analogues, combined with their even incorporation and selective interference, provides an improved method for identifying sites of adenosine protonation in a variety of systems.
• N-modification of 7-Deazapurine nucleoside analogues as Anti-Trypanosoma cruzi and anti-Leishmania agents: Structure-activity relationship exploration and In vivo evaluation
  作者：Cai Lin、Denise da Gama Jaén Batista、Ana Lia Mazzeti、Roberson Donola Girão、Gabriel Melo de Oliveira、Izet Karalic、Fabian Hulpia、Maria de Nazaré C. Soeiro、Louis Maes、Guy Caljon、Serge Van Calenbergh

  DOI：10.1016/j.ejmech.2022.114165

  日期：2022.3
• RAMASAMY, KANDASAMY;IMAMURA, NOBUTAKA;ROBINS, ROLAND K.;REVANKAR, GANAPAT+, J. HETEROCYCL. CHEM., 25,(1988) N, C. 1893-1898
  作者：RAMASAMY, KANDASAMY、IMAMURA, NOBUTAKA、ROBINS, ROLAND K.、REVANKAR, GANAPAT+

  DOI：——

  日期：——