4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-[(1-octa-1,7-diyne)]-7H-pyrrolo[2,3-d]pyrimidine | 178995-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-[(1-octa-1,7-diyne)]-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 1-(2-deoxy-β-D-erythropentofuranosyl)-5-(octa-1,7-diynyl)-1H-pyrrolo[2,3-d]pyrimidin-4-amine；7-deaza-7-(octa-1,7-diynyl)-2'-deoxyadenosine；(2R,3S,5R)-5-(4-amino-5-octa-1,7-diynylpyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 178995-78-3
• 化学式: C₁₉H₂₂N₄O₃
• 分子量: 354.409
• InChiKey: YTNIEKFCPSZFLC-ARFHVFGLSA-N

物化性质

• 沸点：
  667.2±55.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-[(1-octa-1,7-diyne)]-7H-pyrrolo[2,3-d]pyrimidine 在 磷酸三甲酯 、 三正丁胺 、 1,8-双二甲氨基萘 、 三丁基焦磷酸铵 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以2%的产率得到7-deaza-7-(octa-1,7-diynyl)-2'-deoxyadenosine-5'-O-triphosphate
  参考文献：
  名称：

  CLICK CHEMISTRY FOR THE PRODUCTION OF REPORTER MOLECULES

  摘要：

  公开号：

  EP2089343B1
• 作为产物：
  描述：

  4-氯-5-碘-7H-吡咯并[2,3-d]嘧啶 在 氢氧化钾 、 ammonium hydroxide 、 copper(l) iodide 、 四(三苯基膦)钯 、 三(3,6-二氧杂庚基)胺 、 氨 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.33h， 生成 4-amino-7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-[(1-octa-1,7-diyne)]-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Palladium-Catalyzed Cross Coupling of 7-Iodo-2’-deoxytubercidin with Terminal Alkynes

  摘要：

  通过Pd(0)/Cu(I)催化的端炔与7-碘-2'-脱氧结核苷（2d）的交叉耦合反应，制备了7-炔基-2'-脱氧结核苷（7-去氮-2'-脱氧腺苷）7-17。耦合产物包括17α-乙炔睾酮和17α-乙炔雌二醇衍生物（16, 17）。

  DOI：

  10.1055/s-1996-4282

文献信息

• Pyrrolo[2,3-d]Pyrimidine Nucleosides: Synthesis and Antitumor Activity of 7-Substituted 7-Deaza-2′-Deoxyadenosines
  作者：Frank Seela、Matthias Zulauf、Shih-Fong Chen

  DOI：10.1080/15257770008033006

  日期：2000.1

  Abstract A one step synthesis, using the nucleoside 7-iodo-2′-deoxytubercidin (2b) in a Pd(0)/Cu(I)-catalyzed cross coupling reaction furnished a series of 7-alkynyl-2′-deoxytubercidin derivatives. The 7-iodo-, 7-chloro- or 7-bromo 2′-deoxytubercidins 2b-d as well as certain 7-alkynyl derivatives show significant activity against several tumor cell lines, with 7-iodo-2′-deoxytubercidin (2b) as the

  摘要在Pd（0）/ Cu（I）催化的交叉偶联反应中，使用核苷7-碘-2'-脱氧tubercidin（2b）一步合成，得到了一系列7-炔基-2'-deoxytubercidin衍生物。7-碘，7-氯或7-溴2'-脱氧结核菌素2b-d和某些7-炔基衍生物对几种肿瘤细胞系均具有显着活性，其中7-碘-2'-脱氧结核菌素（2b）作为最有效的化合物。
• Azide−Alkyne “Click” Conjugation of 8-Aza-7-deazaadenine-DNA: Synthesis, Duplex Stability, and Fluorogenic Dye Labeling
  作者：Frank Seela、Suresh S. Pujari

  DOI：10.1021/bc100090y

  日期：2010.9.15

  phosphoramidite, and oligonucleotides were synthesized. To evaluate the influence of ligands on the oligonucleotide duplex stability, benzyl azide 4 (nonpolar), and 2′,3′-dideoxy azidothymidine 5 (AZT) (polar) were introduced along with the fluorogenic dyes 2 and 3. DNA duplexes with octa-1,7-diynyl side chains (i.e., containing 1) are more stable than oligonucleotides containing 8-aza-7-deaza-2′-deoxyadenosine

  描述了通过Huisgen-Meldal-Sharpless“点击”反应对DNA进行的内部染料标记。荧光9-叠氮基甲基蒽2和3-叠氮基-7-羟基香豆素3被用于寡核苷酸的后合成功能化结合八-（1,7）-二炔基-8-氮杂-7-脱氮基2'-脱氧腺苷1。通过Sonogashira交叉偶联从相应的7-碘化合物制备核苷1，将其转化为相应的亚磷酰胺，并合成寡核苷酸。要评估配体对寡核苷酸双链体稳定性的影响，请使用叠氮化苄4（非极性）和2'，3'-二脱氧叠氮胸苷5（AZT）（极性）与荧光染料2和3一起引入。具有八-1,7-二炔基侧链（即含有1）的DNA双链体比含有8-aza-7-deaza-2'-脱氧腺苷的寡核苷酸更稳定，这表明该侧链具有空间自由度。蒽残基的单个缀合导致双链体熔化的T m增加9°C 。与7-deazaadenine染料缀合物相反，8-aza-7-deazaadenine缀合物几乎没有荧光猝灭，
• Synthesis of Modified DNA by PCR with Alkyne-Bearing Purines Followed by a Click Reaction
  作者：Philipp M. E. Gramlich、Christian T. Wirges、Johannes Gierlich、Thomas Carell

  DOI：10.1021/ol7026015

  日期：2008.1.1

  Alkyne-bearing deazapurine triphosphates were prepared and successfully incorporated into DNA using the polymerase chain reaction (PCR). The obtained alkyne-labeled DNA was successfully used in a click reaction with galactose azide.

  制备了含炔的三氮杂嘌呤三磷酸，并使用聚合酶链反应（PCR）成功地将其掺入了DNA中。所获得的炔烃标记的DNA已成功用于与半乳糖叠氮化物的点击反应。
• 7-Deazapurine and 8-Aza-7-deazapurine Nucleoside and Oligonucleotide Pyrene “Click” Conjugates: Synthesis, Nucleobase Controlled Fluorescence Quenching, and Duplex Stability
  作者：Sachin A. Ingale、Suresh S. Pujari、Venkata Ramana Sirivolu、Ping Ding、Hai Xiong、Hui Mei、Frank Seela

  DOI：10.1021/jo202103q

  日期：2012.1.6

  7-Deazapurine and 8-aza-7-deazapurine nucleosides related to dA and dG bearing 7-octadiynyl or 7-tripropargylamine side chains as well as corresponding oligonucleotides were synthesized. "Click" conjugation with 1-azidomethyl pyrene (10) resulted in fluorescent derivatives. Octadiynyl conjugates show only monomer fluorescence, while the proximal alignment of pyrene residues in the tripropargylamine derivatives causes excimer emission. 8-Aza-7-deazapurine pyrene 'click" conjugates exhibit fluorescence emission much higher than that of 7-deazapurine derivatives. They are quenched by intramolecular charge transfer between the nucleobase and the dye. Oligonucleotide single strands decorated with two "double clicked" pyrenes show weak or no excimer fluorescence. However, when duplexes carry proximal pyrenes in complementary strands, strong excimer fluorescence is observed. A single replacement of a canonical nucleoside by a pyrene conjugate stabilizes the duplex substantially, most likely by stacking interactions: 6-12 degrees C for duplexes with a modified "adenine" base and 2-6 degrees C for a modified "guanine" base. The favorable photophysical properties of 8-aza-7-deazapurine pyrene conjugates improve the utility of pyrene fluorescence reporters in oligonucleotide sensing as these nucleoside conjugates are not affected by nucleobase induced quenching.