methyl (E)-3-[5-carbamoyl-3-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]imidazol-4-yl]prop-2-enoate | 175545-10-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: methyl (E)-3-[5-carbamoyl-3-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]imidazol-4-yl]prop-2-enoate
• CAS: 175545-10-5
• 化学式: C₁₉H₂₃N₃O₁₀
• 分子量: 453.406
• InChiKey: OZRHKTNGSWVHOX-HPFAKSQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.51
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  175.34
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[5-carbamoyl-3-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]imidazol-4-yl]prop-2-enoate 在 ozone-containing oxygen 、 二甲基硫 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 10.33h， 生成 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide
  参考文献：
  名称：

  Nucleosides and Nucleotides. 140. Synthesis and Antileukemic Activity of 5-Carbon-Substituted 1-β-d-Ribofuflranosylimidazole-4-Carboxamides

  摘要：

  Synthesis of 5-carbon-substituted 1-beta-D-ribofuranosylimidazole-4-carboxamides are described. Treatment of 5-iodo derivative 8 with methyl acrylate in the presence of palladium catalyst gave (E)-5-(2-carbomethoxyvinyl)-1-(2,3,5-tri-O-acetyl- beta-D-ribofuranosyl)imidazole-4-carboxamide (9), followed by appropriate manipulations to afford various 5-carbon-substituted imidazole derivatives 1-7. The antileukemic activities of these imidazole nucleosides are also described.

  DOI：

  10.1080/07328319608002383
• 作为产物：
  描述：

  5-iodo-1-(2,3,5-tri-0-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide 、 丙烯酸甲酯（MA） 在 二(氰基苯)二氯化钯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以65%的产率得到methyl (E)-3-[5-carbamoyl-3-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]imidazol-4-yl]prop-2-enoate
  参考文献：
  名称：

  Nucleosides and Nucleotides. 140. Synthesis and Antileukemic Activity of 5-Carbon-Substituted 1-β-d-Ribofuflranosylimidazole-4-Carboxamides

  摘要：

  Synthesis of 5-carbon-substituted 1-beta-D-ribofuranosylimidazole-4-carboxamides are described. Treatment of 5-iodo derivative 8 with methyl acrylate in the presence of palladium catalyst gave (E)-5-(2-carbomethoxyvinyl)-1-(2,3,5-tri-O-acetyl- beta-D-ribofuranosyl)imidazole-4-carboxamide (9), followed by appropriate manipulations to afford various 5-carbon-substituted imidazole derivatives 1-7. The antileukemic activities of these imidazole nucleosides are also described.

  DOI：

  10.1080/07328319608002383

文献信息

• Nucleosides and nucleotides 179. Ring-expanded purine nucleosides. The synthesis and cytotoxicity of imidazo[4,5-c]azepine nucleosides
  作者：Noriaki Minakawa、Takuma Sasaki、Akira Matsuda

  DOI：10.1016/s0040-4020(98)00832-1

  日期：1998.10

  The synthesis of ring-expanded imidazo[4,5-c]azepine nucleosides (3–6) is described. Treatment of 5-iodoimidazole derivative 9 with methyl acrylate in the presence of a palladium catalyst gave (10), appropriate manipulation of which gave (3). The ring-expanded guanosine derivative 4 was prepared in a manner similar to the synthesis of 3. The ring-expanded inosine derivatives 5 and 6 were obtained from

  描述了扩环的咪唑并[4,5- c ]氮杂氮杂核苷（3–6）的合成。在钯催化剂的存在下用丙烯酸甲酯处理5-碘咪唑衍生物9，得到（10），对其进行适当的操作得到（3）。以类似于3的合成的方式制备环扩的鸟苷衍生物4。从（21）通过钯催化的氢解获得环膨胀的肌苷衍生物5和6。还描述了这些环扩核苷的细胞毒性。
• MATSUDA, AKIRA;MINAKAWA, NORIAKI;UEDA, TOHRU, 15TH SYMP. NUCL. ACIDS CHEM., SAPPORO, SEPT. 19TH - 21ST, 1988, OXFORD; W+
  作者：MATSUDA, AKIRA、MINAKAWA, NORIAKI、UEDA, TOHRU

  DOI：——

  日期：——