monosodium 2-β-ribofuranosylselenazole-4-carboxamide 5'-phosphate | 88268-53-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: monosodium 2-β-ribofuranosylselenazole-4-carboxamide 5'-phosphate
• 英文别名: selenazofurin 5'-monophosphate；2-β-D-ribofuranosylselenazole-4-carboxamide 5'-phosphate；2-(5-O-Phosphono-I(2)-D-ribofuranosyl)-4-selenazolecarboxamide；[(2R,3S,4R,5R)-5-(4-carbamoyl-1,3-selenazol-2-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS: 88268-53-5
• 化学式: C₉H₁₃N₂O₈PSe
• 分子量: 387.145
• InChiKey: HJEPYGYDAPBRRK-DBRKOABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.49
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  monosodium 2-β-ribofuranosylselenazole-4-carboxamide 5'-phosphate 在 三正丁胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成
  参考文献：
  名称：

  Ribavirin, tiazofurin, and selenazofurin: mononucleotides and nicotinamide adenine dinucleotide analogs. Synthesis, structure, and interactions with IMP dehydrogenase

  摘要：

  A series of dinucleotides, analogous to nicotinamide adenine dinucleotide but containing the five-membered base nucleosides tiazofurin (1a), selenazofurin (1b), ribavirin (2), and AICAR (3) in place of nicotinamide ribonucleoside, were prepared in greater than 50% yield by reacting the corresponding nucleotide imidazolidates (6a-d) with adenosine 5'-monophosphate (AMP). The symmetric dinucleotides of tiazofurin (TTD, 8e) and selenazofurin (SSD, 8f) were also prepared by a similar methodology. These dinucleotides were characterized by 1H NMR and fast atom bombardment MS and were evaluated for their inhibitory potency against a partially purified preparation of tumoral inosine monophosphate dehydrogenase (IMPD) from P388 cells. The order of potency found was SAD (8b) greater than TAD (8a) much greater than SSD (8f) congruent to TTD (8e) congruent to RAD (8c) much much greater than ZAD (8d). On kinetic analysis none of the dinucleotides produced competitive inhibition of IMPD with NAD as a variable substrate. In addition to their superior IMPD inhibitory activity, SAD and TAD appear to be the only dinucleotides, besides NAD, that are formed naturally by the NAD pyrophosphorylase from P388 lymphoblasts.

  DOI：

  10.1021/jm00379a018
• 作为产物：
  描述：

  2,3,5-tri-O-benzoyl-β-D-ribofuranosyl-1-carbonitrile 在 吡啶 、 4-二甲氨基吡啶 、 氨 、 水 、 selenium 、 三氯氧磷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 73.0h， 生成 monosodium 2-β-ribofuranosylselenazole-4-carboxamide 5'-phosphate
  参考文献：
  名称：

  2-β-D-呋喃核糖基硒烯唑-4-羧酰胺及其相关衍生物的合成及抗肿瘤活性。

  摘要：

  用硒化氢处理2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖基-1-腈提供了2,5-脱水-3,4,6-三-O-苯甲酰基-D-异壬酰胺（3 ）。用溴丙酮酸乙酯处理化合物3，得到2-（2,3,5-三-O-苯甲酰基-D-呋喃呋喃糖基）硒代唑-4-羧酸乙酯，在氨解后将其转化为2-β-D-呋喃呋喃糖基硒代唑-4。 -羧酰胺（6）及其α-类似物7。核苷6的乙酰化提供2-（2,3,5-三-O-乙酰基-β-D-呋喃呋喃糖基）硒唑-4-羧酰胺，6的磷酸化提供相应的5'-磷酸酯9。化合物6和9分别为被发现对培养中的P388和L1210细胞具有细胞毒性，并有效抵抗小鼠Lewis肺癌。

  DOI：

  10.1021/jm00357a024