4-amino-5-(furan-3-yl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 5'-O-monophosphate sodium salt | 1252859-00-9

• 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: 4-amino-5-(furan-3-yl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 5'-O-monophosphate sodium salt
• 英文别名: sodium;[(2R,3S,4R,5R)-5-[4-amino-5-(furan-3-yl)pyrrolo[2,3-d]pyrimidin-7-yl]-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• CAS: 1252859-00-9
• 化学式: C₁₅H₁₆N₄O₈P*Na
• 分子量: 434.278
• InChiKey: KLGMVMVOFVYTIZ-DNBRLMRSSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.63
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  189
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  3-呋喃硼酸 、 7-iodo-7-deazaadenosine 5'-O-monophosphate 在 trisodium tris(3-sulfophenyl)phosphine 、 palladium diacetate 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 以45%的产率得到4-amino-5-(furan-3-yl)-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 5'-O-monophosphate sodium salt
  参考文献：
  名称：

  Synthesis and Significant Cytostatic Activity of 7-Hetaryl-7-deazaadenosines

  摘要：

  A series of 7-aryl- and 7-hetaryl-7-deazaadenosines were prepared by the cross-coupling reactions of unprotected or protected 7-iodo-7-deazaadenosines with (het)arylboronic acids, stannanes, or zinc halides. Nucleosides bearing 5-membered heterocycles at the position 7 exerted potent in vitro antiproliferative effects against a broad panel of hematological and solid tumor cell lines. Cell cycle analysis indicated profound inhibition of RNA synthesis and induction of apoptosis in treated cells. Intracellular conversion to triphosphates has been detected with active compounds. The triphosphate metabolites showed only a weak inhibitory effect on human RNA polymerase II, suggesting potentially other mechanisms for the inhibition of RNA synthesis and quick onset of apoptosis. Initial in vivo evaluation demonstrated an effect of 7-(2-thienyl)-7-deazaadenine ribonucleoside on the survival rate in syngeneic P388D1 mouse leukemia model.

  DOI：

  10.1021/jm2005173

文献信息

• Synthesis and Significant Cytostatic Activity of 7-Hetaryl-7-deazaadenosines
  作者：Aurelie Bourderioux、Petr Nauš、Pavla Perlíková、Radek Pohl、Iva Pichová、Ivan Votruba、Petr Džubák、Petr Konečný、Marián Hajdúch、Kirsten M. Stray、Ting Wang、Adrian S. Ray、Joy Y. Feng、Gabriel Birkus、Tomas Cihlar、Michal Hocek

  DOI：10.1021/jm2005173

  日期：2011.8.11

  A series of 7-aryl- and 7-hetaryl-7-deazaadenosines were prepared by the cross-coupling reactions of unprotected or protected 7-iodo-7-deazaadenosines with (het)arylboronic acids, stannanes, or zinc halides. Nucleosides bearing 5-membered heterocycles at the position 7 exerted potent in vitro antiproliferative effects against a broad panel of hematological and solid tumor cell lines. Cell cycle analysis indicated profound inhibition of RNA synthesis and induction of apoptosis in treated cells. Intracellular conversion to triphosphates has been detected with active compounds. The triphosphate metabolites showed only a weak inhibitory effect on human RNA polymerase II, suggesting potentially other mechanisms for the inhibition of RNA synthesis and quick onset of apoptosis. Initial in vivo evaluation demonstrated an effect of 7-(2-thienyl)-7-deazaadenine ribonucleoside on the survival rate in syngeneic P388D1 mouse leukemia model.