9-[(N-(2-cyanoethyl)-N-(2-diethoxyphosphorylethyl))-2-aminoethyl]guanine | 1383381-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-[(N-(2-cyanoethyl)-N-(2-diethoxyphosphorylethyl))-2-aminoethyl]guanine
• 英文别名: diethyl 9-[(N-(2-cyanoethyl)-N-(2-phosphonoethyl))-2-aminoethyl]guanine；3-[2-(2-amino-6-oxo-1H-purin-9-yl)ethyl-(2-diethoxyphosphorylethyl)amino]propanenitrile
• CAS: 1383381-94-9
• 化学式: C₁₆H₂₆N₇O₄P
• 分子量: 411.401
• InChiKey: YJNCZDWZCAITGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  148
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-[(N-(2-cyanoethyl)-N-(2-diethoxyphosphorylethyl))-2-aminoethyl]guanine 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  [EN] 6-OXOPURINE PHOSPHORIBOSYLTRANSFERASE INHIBITORS
  [FR] INHIBITEURS DE 6-OXOPURINE PHOSPHORIBOSYLTRANSFÉRASE

  摘要：

  公开号：

  WO2013166545A3
• 作为产物：
  描述：

  diethyl 2-((2-cyanoethyl)(2-hydroxyethyl)amino)ethylphosphonate 在 偶氮二甲酸二异丙酯 、 水 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 9-[(N-(2-cyanoethyl)-N-(2-diethoxyphosphorylethyl))-2-aminoethyl]guanine
  参考文献：
  名称：

  [EN] 6-OXOPURINE PHOSPHORIBOSYLTRANSFERASE INHIBITORS
  [FR] INHIBITEURS DE 6-OXOPURINE PHOSPHORIBOSYLTRANSFÉRASE

  摘要：

  公开号：

  WO2013166545A3

文献信息

• 6-OXOPURINE PHOSPHORIBOSYLTRANSFERASE INHIBITORS
  申请人：THE UNIVERSITY OF QUEENSLAND

  公开号：US20150099722A1

  公开（公告）日：2015-04-09

  The invention relates to compounds which are useful as inhibitors of 6-oxopurine phosphoribosyltransferases such as hypoxanthine-guanine-(xanthine) phosphoribosyltransferase (HG(X)PRT).

  本发明涉及一种化合物，该化合物可用作6-氧嘌呤磷酸核糖转移酶的抑制剂，例如次黄嘌呤鸟嘌呤-(黄嘌呤)磷酸核糖转移酶（HG（X）PRT）。
• [EN] 6-OXOPURINE PHOSPHORIBOSYLTRANSFERASE INHIBITORS<br/>[FR] INHIBITEURS DE 6-OXOPURINE PHOSPHORIBOSYLTRANSFÉRASE
  申请人：UNIV QUEENSLAND

  公开号：WO2013166545A3

  公开（公告）日：2015-03-05
• Aza-acyclic Nucleoside Phosphonates Containing a Second Phosphonate Group As Inhibitors of the Human, <i>Plasmodium falciparum</i> and <i>vivax</i> 6-Oxopurine Phosphoribosyltransferases and Their Prodrugs As Antimalarial Agents
  作者：Dianne T. Keough、Dana Hocková、Zlatko Janeba、Tzu-Hsuan Wang、Lieve Naesens、Michael D. Edstein、Marina Chavchich、Luke W. Guddat

  DOI：10.1021/jm501416t

  日期：2015.1.22

  Hypoxanthineguanine[xanthine] phosphoribosyltransferase (HG[X]PRT) is considered an important target for antimalarial chemotherapy as it is the only pathway for the synthesis of the purine nucleoside monophosphates required for DNA/RNA production. Thus, inhibition of this enzyme should result in cessation of replication. The aza-acyclic nucleoside phosphonates (aza-ANPs) are good inhibitors of Plasmodium falciparum HGXPRT (PfHGXPRT), with K-i values as low as 0.08 and 0.01 mu M for Plasmodium vivax HGPRT (PvHGPRT). Prodrugs of these aza-ANPs exhibit antimalarial activity against Pf lines with IC50 values (0.8-6.0 mu M) and have low cytotoxicity against human cells. Crystal structures of six of these compounds in complex with human HGPRT have been determined. These suggest that the different affinities of these aza-ANPs could be due to the flexibility of the loops surrounding the active site as well as the flexibility of the inhibitors, allowing them to adapt to fit into three binding pockets of the enzyme(s).
• EP2847201B1
  申请人：——

  公开号：EP2847201B1

  公开（公告）日：2017-08-16
• US9200020B2
  申请人：——

  公开号：US9200020B2

  公开（公告）日：2015-12-01