3-amino-1H-pyrazolo[3,4-d]pyrimidin-6-ol | 1404307-27-2

• 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: 3-amino-1H-pyrazolo[3,4-d]pyrimidin-6-ol
• 英文别名: 3-Amino-2,7-dihydropyrazolo[3,4-d]pyrimidin-6-one；3-amino-2,7-dihydropyrazolo[3,4-d]pyrimidin-6-one
• CAS: 1404307-27-2
• 化学式: C₅H₅N₅O
• 分子量: 151.128
• InChiKey: BPJWFHIIZIMMJF-UHFFFAOYSA-N

物化性质

• 密度：
  2.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-1H-pyrazolo[3,4-d]pyrimidin-6-ol 在 盐酸 、 三氯氧磷 作用下， 以 N,N-二甲基乙酰胺 、 水 、 正丁醇 为溶剂， 反应 5.83h， 生成 1-[3-[(3-amino-2H-pyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-3-[(1R)-1-phenylethyl]urea
  参考文献：
  名称：

  Discovery of N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine derivatives as novel CK1 inhibitors using common-feature pharmacophore model based virtual screening and hit-to-lead optimization

  摘要：

  Aberrant activation of casein kinase 1 (CK1) has been demonstrated to be implicated in the pathogenesis of cancer and various central nervous system disorders. Discovery of CK1 inhibitors has thus attracted much attention in recent years. In this account, we describe the discovery of N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine derivatives as novel CK1 inhibitors. An optimal common-feature pharmacophore hypothesis, termed Hypo2, was firstly generated, followed by virtual screening using Hypo2 against several chemical databases. One of the best hit compounds, N6-(4-chlorophenyl)-1H-pyrazolo [3,4-d]pyrimidine-3,6-diamine, was chosen for the subsequent hit-to-lead optimization under the guide of Hypo2, which led to the discovery of a new lead compound (1-(3-(3-amino-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-3-(3-chloro-4-fluorophenyl)urea) that potently inhibits CK1 with an IC50 value of 78 nM. (c) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.007
• 作为产物：
  描述：

  4-氯-2-甲硫基嘧啶-5-腈 在 盐酸 、 水 、 一水合肼 作用下， 以 乙醇 、 正丁醇 为溶剂， 反应 0.5h， 生成 3-amino-1H-pyrazolo[3,4-d]pyrimidin-6-ol
  参考文献：
  名称：

  Discovery of N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine derivatives as novel CK1 inhibitors using common-feature pharmacophore model based virtual screening and hit-to-lead optimization

  摘要：

  Aberrant activation of casein kinase 1 (CK1) has been demonstrated to be implicated in the pathogenesis of cancer and various central nervous system disorders. Discovery of CK1 inhibitors has thus attracted much attention in recent years. In this account, we describe the discovery of N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine derivatives as novel CK1 inhibitors. An optimal common-feature pharmacophore hypothesis, termed Hypo2, was firstly generated, followed by virtual screening using Hypo2 against several chemical databases. One of the best hit compounds, N6-(4-chlorophenyl)-1H-pyrazolo [3,4-d]pyrimidine-3,6-diamine, was chosen for the subsequent hit-to-lead optimization under the guide of Hypo2, which led to the discovery of a new lead compound (1-(3-(3-amino-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)phenyl)-3-(3-chloro-4-fluorophenyl)urea) that potently inhibits CK1 with an IC50 value of 78 nM. (c) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.007