2-amino-5-phenyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one | 1536112-45-4

• 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-amino-5-phenyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one
• 英文别名: 2-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-phenyl-3H-pyrrolo[2,3-d]pyrimidin-4-one；2-amino-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-phenyl-3H-pyrrolo[2,3-d]pyrimidin-4-one
• CAS: 1536112-45-4
• 化学式: C₁₇H₁₈N₄O₅
• 分子量: 358.354
• InChiKey: KHJPCHIYZJCQOY-XNIJJKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  142
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-amino-5-phenyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one 在 磷酸三甲酯 、 三正丁胺 、 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， 反应 2.0h， 以30%的产率得到7-phenyl-7-deazaguanosine-5’-O-triphosphate sodium salt
  参考文献：
  名称：

  通过T7 RNA聚合酶酶促合成碱基修饰的RNA。对5取代的嘧啶和7取代的7-脱氮嘌呤核苷三磷酸核苷作为底物的系统研究和比较†

  摘要：

  我们通过核苷的交叉偶联反应，随后的三磷酸化反应或通过卤化的直接交叉偶联反应，合成了一个小库，该库包含十八个带有甲基，乙炔基，苯基，苯并呋喃基或二苯并呋喃基的5-取代的嘧啶或7-取代的7-脱氮嘌呤核苷三磷酸核苷三磷酸。我们系统地研究了修饰对T7 RNA聚合酶催化的修饰RNA合成效率的影响，发现修饰较小的修饰ATP，UTP和CTP类似物是RNA合成的良好底物和基石，即使在困难的序列中掺入了多个修饰的核苷酸。ATP和GTP的大体积二苯并呋喃基衍生物不是RNA聚合酶的底物。对于修饰的GTP类似物，需要使用特殊的启动子和GMP作为引发剂的改良程序，才能获得有效的RNA合成。修饰的RNA的T7 RNA聚合酶合成可以非常有效地用于修饰的RNA的合成，但是该方法在转录本的前三个核苷酸的序列中有限制，该转录本的前三个核苷酸必须在+1位包含一个未修饰的G。

  DOI：

  10.1039/c8ob01498a
• 作为产物：
  描述：

  2-amino-4-methoxy-5-phenyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 40.0h， 以56%的产率得到2-amino-5-phenyl-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Synthesis, Cytostatic, Antimicrobial, and Anti-HCV Activity of 6-Substituted 7-(Het)aryl-7-deazapurine Ribonucleosides

  摘要：

  A series of 80 7-(het)aryl- and 7-ethyny1-7-deazapurine ribonucleosides bearing a methoxy, methylsulfanyl, methylamino, dimethylamino, methyl, or oxo group at position 6, or 2,6-disubstituted derivatives bearing a methyl or amino group at position 2, were prepared, and the biological activity of the compounds was studied and compared with that of the parent 7-(het)ary1-7-deazaadenosine series. Several of the compounds, in particular 6-substituted 7-deazapurine derivatives bearing a furyl or ethynyl group at position 7, were significantly cytotoxic at low nanomolar concentrations whereas most were much less potent or inactive. Promising activity was observed with some compounds against Mycobacterium bovis and also against hepatitis C virus in a replicon assay.

  DOI：

  10.1021/jm4018948

文献信息

• Enzymatic synthesis of base-modified RNA by T7 RNA polymerase. A systematic study and comparison of 5-substituted pyrimidine and 7-substituted 7-deazapurine nucleoside triphosphates as substrates
  作者：Nemanja Milisavljevič、Pavla Perlíková、Radek Pohl、Michal Hocek

  DOI：10.1039/c8ob01498a

  日期：——

  initiator needed to be used to obtain efficient RNA synthesis. The T7 RNA polymerase synthesis of modified RNA can be very efficiently used for synthesis of modified RNA but the method has constraints in the sequence of the first three nucleotides of the transcript, which must contain a non-modified G in the +1 position.

  我们通过核苷的交叉偶联反应，随后的三磷酸化反应或通过卤化的直接交叉偶联反应，合成了一个小库，该库包含十八个带有甲基，乙炔基，苯基，苯并呋喃基或二苯并呋喃基的5-取代的嘧啶或7-取代的7-脱氮嘌呤核苷三磷酸核苷三磷酸。我们系统地研究了修饰对T7 RNA聚合酶催化的修饰RNA合成效率的影响，发现修饰较小的修饰ATP，UTP和CTP类似物是RNA合成的良好底物和基石，即使在困难的序列中掺入了多个修饰的核苷酸。ATP和GTP的大体积二苯并呋喃基衍生物不是RNA聚合酶的底物。对于修饰的GTP类似物，需要使用特殊的启动子和GMP作为引发剂的改良程序，才能获得有效的RNA合成。修饰的RNA的T7 RNA聚合酶合成可以非常有效地用于修饰的RNA的合成，但是该方法在转录本的前三个核苷酸的序列中有限制，该转录本的前三个核苷酸必须在+1位包含一个未修饰的G。
• Synthesis, Cytostatic, Antimicrobial, and Anti-HCV Activity of 6-Substituted 7-(Het)aryl-7-deazapurine Ribonucleosides
  作者：Petr Nauš、Olga Caletková、Petr Konečný、Petr Džubák、Kateřina Bogdanová、Milan Kolář、Jana Vrbková、Lenka Slavětínská、Eva Tloušt’ová、Pavla Perlíková、Marián Hajdúch、Michal Hocek

  DOI：10.1021/jm4018948

  日期：2014.2.13

  A series of 80 7-(het)aryl- and 7-ethyny1-7-deazapurine ribonucleosides bearing a methoxy, methylsulfanyl, methylamino, dimethylamino, methyl, or oxo group at position 6, or 2,6-disubstituted derivatives bearing a methyl or amino group at position 2, were prepared, and the biological activity of the compounds was studied and compared with that of the parent 7-(het)ary1-7-deazaadenosine series. Several of the compounds, in particular 6-substituted 7-deazapurine derivatives bearing a furyl or ethynyl group at position 7, were significantly cytotoxic at low nanomolar concentrations whereas most were much less potent or inactive. Promising activity was observed with some compounds against Mycobacterium bovis and also against hepatitis C virus in a replicon assay.