3'-(4-mercapto-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)propanamide | 188727-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3'-(4-mercapto-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)propanamide
• CAS: 188727-04-0
• 化学式: C₁₄H₁₃N₅OS₂
• 分子量: 331.422
• InChiKey: SYBVGMUTBUATTO-UHFFFAOYSA-N

物化性质

• 沸点：
  623.4±61.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  86.69
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3'-(4-mercapto-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)propanamide 在 sodium hydroxide 、 氨 作用下， 以 乙醇 为溶剂， 反应 72.5h， 生成 3'-(4-amino-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)propanamide
  参考文献：
  名称：

  1-Phenylpyrazolo[3,4-d]pyrimidines as adenosine antagonists: the effects of substituents at C4 and C6

  摘要：

  Forty-two 1-phenyl-pyrazolo[3,4-d]pyrimidines substituted at C6 with thioethers containing distal amide substituents and substituted at C4 with thiol, thiomethyl or amino were synthesized and tested for adenosine A(1) and A(2a) receptor binding. Compared with a thiol at C4, both S-methylation and conversion to an amino resulted in increased affinity at both receptors with the C4 amino compounds having the highest affinity. The C-4 region of the receptor consists of an alkyl pocket containing a hydrogen-bonding site. The study established that for high affinity at both the A(1) and A(2a) adenosine receptors the distal amide should be separated from the C6 thiol by only one carbon. In this study, 2'-(4-amino-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)- N-ethyl-ethanamide (4b) had the highest affinity at the A(1) receptor with a K-i of 12.1 nM while 2'-(4-amino-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)ethanamide (4a) had the highest affinity at the A(2a) receptor with a K-i of 44.9 nM. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00240-4
• 作为产物：
  描述：

  3-溴丙胺 、 1-phenylpyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dithione 在 吡啶 作用下， 反应 3.0h， 以68%的产率得到3'-(4-mercapto-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)propanamide
  参考文献：
  名称：

  1-Phenylpyrazolo[3,4-d]pyrimidines as adenosine antagonists: the effects of substituents at C4 and C6

  摘要：

  Forty-two 1-phenyl-pyrazolo[3,4-d]pyrimidines substituted at C6 with thioethers containing distal amide substituents and substituted at C4 with thiol, thiomethyl or amino were synthesized and tested for adenosine A(1) and A(2a) receptor binding. Compared with a thiol at C4, both S-methylation and conversion to an amino resulted in increased affinity at both receptors with the C4 amino compounds having the highest affinity. The C-4 region of the receptor consists of an alkyl pocket containing a hydrogen-bonding site. The study established that for high affinity at both the A(1) and A(2a) adenosine receptors the distal amide should be separated from the C6 thiol by only one carbon. In this study, 2'-(4-amino-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)- N-ethyl-ethanamide (4b) had the highest affinity at the A(1) receptor with a K-i of 12.1 nM while 2'-(4-amino-1-phenylpyrazolo[3,4-d]pyrimidin-6-ylthio)ethanamide (4a) had the highest affinity at the A(2a) receptor with a K-i of 44.9 nM. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00240-4