diethyl [(3R)-4-hydroxy-3-[({4-hydroxy-5Hpyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]butyl]phosphonate hydrochloride | 1404216-96-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: diethyl [(3R)-4-hydroxy-3-[({4-hydroxy-5Hpyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]butyl]phosphonate hydrochloride
• 英文别名: diethyl [(3R)-4-hydroxy-3-[({4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]butyl]phosphonate hydrochloride
• CAS: 1404216-96-1
• 化学式: C₁₅H₂₅N₄O₅P*ClH
• 分子量: 408.822
• InChiKey: XQCSZCZBTUXIJK-UTONKHPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  129.59
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diethyl [(3R)-4-hydroxy-3-[({4-hydroxy-5Hpyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]butyl]phosphonate hydrochloride 在 水 、 氢溴酸 作用下， 反应 4.0h， 以71%的产率得到[(3R)-4-hydroxy-3-[({4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]butyl]phosphonic acid hydrobromide
  参考文献：
  名称：

  Acyclic phosph(on)ate inhibitors of Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase

  摘要：

  The pathogenic protozoa responsible for malaria lack enzymes for the de novo synthesis of purines and rely on purine salvage from the host. In Plasmodium falciparum (Pf), hypoxanthine-guanine-xanthine phosphoribosyltransferase (HGXPRT) converts hypoxanthine to inosine monophosphate and is essential for purine salvage making the enzyme an anti-malarial drug target. We have synthesized a number of simple acyclic aza-C-nucleosides and shown that some are potent inhibitors of Pf HGXPRT while showing excellent selectivity for the Pf versus the human enzyme. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.016
• 作为产物：
  描述：

  4-(tert-butoxy)-2-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carbaldehyde 在 盐酸 、 2-甲基吡啶-N-甲硼烷 、 palladium 10% on activated carbon 、 水 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 19.17h， 生成 diethyl [(3R)-4-hydroxy-3-[({4-hydroxy-5Hpyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]butyl]phosphonate hydrochloride
  参考文献：
  名称：

  Acyclic phosph(on)ate inhibitors of Plasmodium falciparum hypoxanthine-guanine-xanthine phosphoribosyltransferase

  摘要：

  The pathogenic protozoa responsible for malaria lack enzymes for the de novo synthesis of purines and rely on purine salvage from the host. In Plasmodium falciparum (Pf), hypoxanthine-guanine-xanthine phosphoribosyltransferase (HGXPRT) converts hypoxanthine to inosine monophosphate and is essential for purine salvage making the enzyme an anti-malarial drug target. We have synthesized a number of simple acyclic aza-C-nucleosides and shown that some are potent inhibitors of Pf HGXPRT while showing excellent selectivity for the Pf versus the human enzyme. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.016