6-amino-1-(hydroxyethoxymethyl)-4(5H)-oxopyrazolo[3,4-d]pyrimidine | 96445-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 6-amino-1-(hydroxyethoxymethyl)-4(5H)-oxopyrazolo[3,4-d]pyrimidine
• 英文别名: 6-amino-1,5-dihydro-1-<(2-hydroxyethoxy)-methyl>-4H-pyrazolo<3,4-d>pyrimidin-4-one；6-amino-1-(2-hydroxyethoxymethyl)-5H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS: 96445-97-5
• 化学式: C₈H₁₁N₅O₃
• 分子量: 225.207
• InChiKey: XGKAEIFKPVRTCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,6-dimethylthio-1-hydroxyethoxymethyl-pyrazolo[3,4-d]pyrimidine 在 sodium hydroxide 、 氨 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 78.0h， 生成 6-amino-1-(hydroxyethoxymethyl)-4(5H)-oxopyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Acyclic Pyrazolo[3,4- d ]Pyrimidine Nucleoside as Potential Leishmaniostatic Agent *

  摘要：

  A new synthesis of 6-amino-1-hydroxyethoxymethyl-4(5H)-oxopyrazolo[3,4-d] pyrimidine ( 4) has been mentioned. Compound 4 exhibited inhibition of amastigotes of Leishmania donovani to the extent of 89% at 30 mu g/mL, whereas iso-guanine analogue 5 had the inhibition only to the extent of 52.8% at 100 mu g/mL in vitro. In hamster model the maximum inhibitory response for compound 4 against amastigotes multiplication was observed to be 94% at 50 mg/kg single dose for 5 consecutive days.

  DOI：

  10.1081/15257770500379017

文献信息

• Modifications on the heterocyclic base of acyclovir: syntheses and antiviral properties
  作者：Lilia M. Beauchamp、Bart L. Dolmatch、Howard J. Schaeffer、Peter Collins、D. J. Bauer、Paul M. Keller、James A. Fyfe

  DOI：10.1021/jm00146a002

  日期：1985.8

  A group of compounds was prepared in which variations of the ring portion of the acyclovir (ACV) structure were made. These modifications included monocyclic (isocytosine, triazole, imidazole), bicyclic (8-azapurine, pyrrolo[2,3-d]pyrimidine, pyrazolo[3,4-d]pyrimidine) and tricyclic (linear benzoguanine) congeners. The derivatives were evaluated against herpes simplex virus type 1 (HSV-1) by the plaque-inhibition and plaque-reduction methods with only the 8-azapurine analogue 28 showing some activity. In a test measuring the ability of these compounds to inhibit the HSV-1 thymidine kinase, 28 and the tricyclic derivative 38 exhibited competition with ACV for binding to the enzyme. The inability of the group to exert significant antiherpetic action is attributed to their lack of phosphorylation to the requisite triphosphate stage.
• Acyclic Pyrazolo[3,4- d ]Pyrimidine Nucleoside as Potential Leishmaniostatic Agent *
  作者：A. Hasan、M. Satyanarayana、A. Mishra、D. Bhakuni、Ram Pratap、A. Dube、P. Guru

  DOI：10.1081/15257770500379017

  日期：2006.1.1

  A new synthesis of 6-amino-1-hydroxyethoxymethyl-4(5H)-oxopyrazolo[3,4-d] pyrimidine ( 4) has been mentioned. Compound 4 exhibited inhibition of amastigotes of Leishmania donovani to the extent of 89% at 30 mu g/mL, whereas iso-guanine analogue 5 had the inhibition only to the extent of 52.8% at 100 mu g/mL in vitro. In hamster model the maximum inhibitory response for compound 4 against amastigotes multiplication was observed to be 94% at 50 mg/kg single dose for 5 consecutive days.