Phosphoric acid mono-((2R,3S,4R,5R)-3-hydroxy-4-(3-methoxy-benzoylamino)-5-{6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl) ester | 332079-08-0

• 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: Phosphoric acid mono-((2R,3S,4R,5R)-3-hydroxy-4-(3-methoxy-benzoylamino)-5-{6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl) ester
• 英文别名: ((2R,3S,4R,5R)-3-hydroxy-4-(3-methoxybenzamido)-5-(6-(naphthalen-1-ylmethylamino)-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl dihydrogen phosphate；[(2R,3S,4R,5R)-3-hydroxy-4-[(3-methoxybenzoyl)amino]-5-[6-(naphthalen-1-ylmethylamino)purin-9-yl]oxolan-2-yl]methyl dihydrogen phosphate
• CAS: 332079-08-0
• 化学式: C₂₉H₂₉N₆O₈P
• 分子量: 620.558
• InChiKey: WCJVICQJLSYOTE-BYHVZLFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  44
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  190
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Phosphoric acid mono-((2R,3S,4R,5R)-3-hydroxy-4-(3-methoxy-benzoylamino)-5-{6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl) ester 在 magnesium sulfate 、 N,N'-二环己基碳二亚胺 、 manganese(ll) chloride 作用下， 以 水 、 formamide 、 叔丁醇 为溶剂， 反应 34.0h， 生成 C₄₀H₄₂N₈O₁₅P₂
  参考文献：
  名称：

  A disubstituted NAD + analogue is a nanomolar inhibitor of trypanosomal glyceraldehyde-3-phosphate dehydrogenase

  摘要：

  N-6-Naphthalenemethyl-2'-methoxybenzamido-beta -NAD(+), a derivative of a low micromolar first-generation inhibitor of trypanosomal glyceraldehyde phosphate dehydrogenase (GAPDH), was synthesized, taking advantage of methodology for the selective phosphitylation of nucleosides. The compound was found to be a poor alternate cosubstrate for GAPDH, but an extremely potent inhibitor. Although intended for use in crystallization trials, the analogue presents possibilities for further drug design. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00608-9
• 作为产物：
  描述：

  N⁶-(1-naphthalenemethyl)-2'-deoxy-2'-(3-methoxybenzamido)adenosine 在 叔丁基过氧化氢 、 ammonium hydroxide 、 5-(乙硫基)-1H-四唑 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 17.83h， 生成 Phosphoric acid mono-((2R,3S,4R,5R)-3-hydroxy-4-(3-methoxy-benzoylamino)-5-{6-[(naphthalen-1-ylmethyl)-amino]-purin-9-yl}-tetrahydro-furan-2-ylmethyl) ester
  参考文献：
  名称：

  A disubstituted NAD + analogue is a nanomolar inhibitor of trypanosomal glyceraldehyde-3-phosphate dehydrogenase

  摘要：

  N-6-Naphthalenemethyl-2'-methoxybenzamido-beta -NAD(+), a derivative of a low micromolar first-generation inhibitor of trypanosomal glyceraldehyde phosphate dehydrogenase (GAPDH), was synthesized, taking advantage of methodology for the selective phosphitylation of nucleosides. The compound was found to be a poor alternate cosubstrate for GAPDH, but an extremely potent inhibitor. Although intended for use in crystallization trials, the analogue presents possibilities for further drug design. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00608-9