4-carboxamido-2-(2',3'-isopropylidene-β-D-ribofuranosyl)thiazolyl(5'->5')adenosine pyrophosphate | 85221-13-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 4-carboxamido-2-(2',3'-isopropylidene-β-D-ribofuranosyl)thiazolyl(5'->5')adenosine pyrophosphate
• CAS: 85221-13-2
• 化学式: C₂₂H₂₉N₇O₁₄P₂S
• 分子量: 709.524
• InChiKey: VUHYDQGEYGYYFK-VJOGCJHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.51
• 重原子数：
  46.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  305.27
• 氢给体数：
  6.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  4-carboxamido-2-(2',3'-isopropylidene-β-D-ribofuranosyl)thiazolyl(5'->5')adenosine pyrophosphate 在 溶剂黄146 作用下， 反应 0.42h， 以1.7 mg的产率得到噻唑-4-甲酰胺腺嘌呤二核苷酸
  参考文献：
  名称：

  Synthesis of thiazole-4-carboxamide adenine dinucleotide. A powerful inhibitor of IMP dehydrogenase

  摘要：

  The chemical synthesis of thiazole-4-carboxamide adenine dinucleotide (TAD), previously identified as the active anabolite of the oncolytic 2-beta-D-ribofuranosylthiazole-4-carboxamide (TR), has been achieved by three different approaches: (1) incubation of adenosine 5'-monophosphate (AMP) and 2-beta-D-ribofuranosylthiazole-4-carboxamide 5'-monophosphate (TRMP) with excess DCC in aqueous pyridine, (2) reaction of adenosine 5'-phosphoromorpholidate with TRMP in pyridine, and (3) reaction of adenosine-5'-phosphoric di-n-butylphosphinothioic anhydride with TRMP in the presence of AgNO3. While the first approach produced only traces of TAD, the last two afforded 31 and 16% yields, respectively, of isolated TAD. The synthetic material was indistinguishable from biosynthesized TAD as judged by its HPLC behavior, NMR, UV and mass spectra, enzymatic resistance to alkaline phosphatase and susceptibility to venom phosphodiesterase, IMP dehydrogenase inhibitory activity, and cytotoxicity. TAD and TR were equally effective against murine P388 leukemia when employed at equimolar doses.

  DOI：

  10.1021/jm00360a025
• 作为产物：
  描述：

  2-[2,3-O-(1-甲基乙亚基)-beta-D-呋喃核糖基]-4-噻唑甲酰胺 在 三辛胺 、 三氯氧磷 作用下， 以 various solvent(s) 为溶剂， 反应 5.0h， 生成 4-carboxamido-2-(2',3'-isopropylidene-β-D-ribofuranosyl)thiazolyl(5'->5')adenosine pyrophosphate
  参考文献：
  名称：

  Synthesis of thiazole-4-carboxamide adenine dinucleotide. A powerful inhibitor of IMP dehydrogenase

  摘要：

  The chemical synthesis of thiazole-4-carboxamide adenine dinucleotide (TAD), previously identified as the active anabolite of the oncolytic 2-beta-D-ribofuranosylthiazole-4-carboxamide (TR), has been achieved by three different approaches: (1) incubation of adenosine 5'-monophosphate (AMP) and 2-beta-D-ribofuranosylthiazole-4-carboxamide 5'-monophosphate (TRMP) with excess DCC in aqueous pyridine, (2) reaction of adenosine 5'-phosphoromorpholidate with TRMP in pyridine, and (3) reaction of adenosine-5'-phosphoric di-n-butylphosphinothioic anhydride with TRMP in the presence of AgNO3. While the first approach produced only traces of TAD, the last two afforded 31 and 16% yields, respectively, of isolated TAD. The synthetic material was indistinguishable from biosynthesized TAD as judged by its HPLC behavior, NMR, UV and mass spectra, enzymatic resistance to alkaline phosphatase and susceptibility to venom phosphodiesterase, IMP dehydrogenase inhibitory activity, and cytotoxicity. TAD and TR were equally effective against murine P388 leukemia when employed at equimolar doses.

  DOI：

  10.1021/jm00360a025