2-(6-amino-8-((E)-4-methylstyryl)-9H-purin-9-yl )-5-(hydroxymethyl)tetrahydrofuran-3,4-diol | 1492667-02-3

• 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: 2-(6-amino-8-((E)-4-methylstyryl)-9H-purin-9-yl )-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• 英文别名: (2R,3R,4S,5R)-2-[6-amino-8-[(E)-2-(4-methylphenyl)ethenyl]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 1492667-02-3
• 化学式: C₁₉H₂₁N₅O₄
• 分子量: 383.407
• InChiKey: QMYZHPNVTLSYJR-VFIQZALSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  反-2-(4-甲苯基)乙烯基硼酸 、 8-bromoadenosine 在 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以27%的产率得到2-(6-amino-8-((E)-4-methylstyryl)-9H-purin-9-yl )-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Rules for the Design of Highly Fluorescent Nucleoside Probes: 8-(Substituted Cinnamyl)-Adenosine Analogues

  摘要：

  Currently, there are no tools that can help the design of useful fluorescent analogues. Hence, we synthesized a series of 8-(substituted cinnamy1)-adenosine analogues, 5-17, and established a relationship between their structure and fluorescence properties. We attempted to find a correlation between maximum emission wavelengths (lambda(em)) of 5-17 or their quantum yields (phi), and Hammett constants (sigma(p) and sigma(m)) of the substituent on the cinnamyl moiety. A linear correlation was observed at low-medium sigma values, but not at high a values (>= 0.7). Next, we explored correlation between lambda(em) and phi of 5-17 and computed HOMO and LUMO energy levels of fragments of 5-17, i.e., 8-vinyl 9-Me-adenine (fluorescent molecule), 18, and substituted toluene rings (fluoresence modulators), 19-30. High phi correlated with relatively close LUMO levels of 19-30 and 18 (-0.076 to 0.003 eV). The electron density of LUMO of nitro analogues 9 and 15 is localized on the aryl ring only, which explains their low phi. Calculation of HOMO LUMO gap of 5-17 enables accurate prediction of the lambda(abs) for a planned analogue, and LUMO levels of an aryl moiety vs 8-vinyl 9-Me-adenine, allows the prediction of high or low phi. These findings lay the ground for prediction of fluorescence properties of additional analogues having a similar structure.

  DOI：

  10.1021/jo402050x

文献信息

• Rules for the Design of Highly Fluorescent Nucleoside Probes: 8-(Substituted Cinnamyl)-Adenosine Analogues
  作者：Lital Zilbershtein-Shklanovsky、Michal Weitman、Dan Thomas Major、Bilha Fischer

  DOI：10.1021/jo402050x

  日期：2013.12.6

  Currently, there are no tools that can help the design of useful fluorescent analogues. Hence, we synthesized a series of 8-(substituted cinnamy1)-adenosine analogues, 5-17, and established a relationship between their structure and fluorescence properties. We attempted to find a correlation between maximum emission wavelengths (lambda(em)) of 5-17 or their quantum yields (phi), and Hammett constants (sigma(p) and sigma(m)) of the substituent on the cinnamyl moiety. A linear correlation was observed at low-medium sigma values, but not at high a values (>= 0.7). Next, we explored correlation between lambda(em) and phi of 5-17 and computed HOMO and LUMO energy levels of fragments of 5-17, i.e., 8-vinyl 9-Me-adenine (fluorescent molecule), 18, and substituted toluene rings (fluoresence modulators), 19-30. High phi correlated with relatively close LUMO levels of 19-30 and 18 (-0.076 to 0.003 eV). The electron density of LUMO of nitro analogues 9 and 15 is localized on the aryl ring only, which explains their low phi. Calculation of HOMO LUMO gap of 5-17 enables accurate prediction of the lambda(abs) for a planned analogue, and LUMO levels of an aryl moiety vs 8-vinyl 9-Me-adenine, allows the prediction of high or low phi. These findings lay the ground for prediction of fluorescence properties of additional analogues having a similar structure.