[4-(4-Benzo[1,3]dioxol-5-ylmethyl-piperazin-1-yl)-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-dimethyl-amine | 461670-50-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: [4-(4-Benzo[1,3]dioxol-5-ylmethyl-piperazin-1-yl)-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-dimethyl-amine
• 英文别名: 4-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-1-tert-butyl-N,N-dimethylpyrazolo[3,4-d]pyrimidin-6-amine
• CAS: 461670-50-8
• 化学式: C₂₃H₃₁N₇O₂
• 分子量: 437.545
• InChiKey: NNBFNGLFIGYHGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [4-(4-Benzo[1,3]dioxol-5-ylmethyl-piperazin-1-yl)-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-dimethyl-amine 在 甲酸 作用下， 以70%的产率得到4-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-N,N-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine
  参考文献：
  名称：

  Pyrazolopyrimidines: synthesis, effect on histamine release from rat peritoneal mast cells and cytotoxic activity

  摘要：

  A series of 1H-pyrazolo[3,4-d]pyrimidines (3-6) substituted at positions 1 (R-1 = Ph, H, tert-butyl and ribosetribenzoate), 4 (R-2 = chlorine, nitrogen and oxygen nucleophiles), and 6 (dimethylamino) have been synthesized and their effect on the release of histamine from rat peritoneal mast cells measured. After chemical stimulation, (polymer 48/80), several compounds (i.e. 3b, 4a, 4b, 4d, 4g, 5a), produce inhibition two to three times higher (40-60%) than DSCG but this action is lower after preincubation. 4b (R-1 = Ph, R-2 = NHCH2Ph; 50-70% inhibition) and 5a (R-1 = H, R-2 = OMe, 50-55% inhibition) are the most active ones in both experiments. With ovoalbumin as stimulus, several pyrazolopyrimidines show inhibition similar to DSCG, the most active compounds being 6a-d (IC50 = 12-16 muM; R-1 = ribosetribenzoate, R-2 = methoxy and amino), Compounds 4e (R-1 = t-butyl, R-2 = OMe) and 4g (R-1 = t-butyl, R-2 = piperidino) are inducers of the release of histamine (60 and 150% increase). Compounds 4b and 4e showed cytotoxic activity (IC50 =1 mug/ml) to HT-29 human colon cancer cells. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01225-9
• 作为产物：
  描述：

  5-氨基-4-氰基-1-叔丁基吡唑 在 盐酸 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 74.0h， 生成 [4-(4-Benzo[1,3]dioxol-5-ylmethyl-piperazin-1-yl)-1-tert-butyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl]-dimethyl-amine
  参考文献：
  名称：

  Pyrazolopyrimidines: synthesis, effect on histamine release from rat peritoneal mast cells and cytotoxic activity

  摘要：

  A series of 1H-pyrazolo[3,4-d]pyrimidines (3-6) substituted at positions 1 (R-1 = Ph, H, tert-butyl and ribosetribenzoate), 4 (R-2 = chlorine, nitrogen and oxygen nucleophiles), and 6 (dimethylamino) have been synthesized and their effect on the release of histamine from rat peritoneal mast cells measured. After chemical stimulation, (polymer 48/80), several compounds (i.e. 3b, 4a, 4b, 4d, 4g, 5a), produce inhibition two to three times higher (40-60%) than DSCG but this action is lower after preincubation. 4b (R-1 = Ph, R-2 = NHCH2Ph; 50-70% inhibition) and 5a (R-1 = H, R-2 = OMe, 50-55% inhibition) are the most active ones in both experiments. With ovoalbumin as stimulus, several pyrazolopyrimidines show inhibition similar to DSCG, the most active compounds being 6a-d (IC50 = 12-16 muM; R-1 = ribosetribenzoate, R-2 = methoxy and amino), Compounds 4e (R-1 = t-butyl, R-2 = OMe) and 4g (R-1 = t-butyl, R-2 = piperidino) are inducers of the release of histamine (60 and 150% increase). Compounds 4b and 4e showed cytotoxic activity (IC50 =1 mug/ml) to HT-29 human colon cancer cells. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01225-9

文献信息

• Pyrazolopyrimidines: synthesis, effect on histamine release from rat peritoneal mast cells and cytotoxic activity
  作者：J Quintela

  DOI：10.1016/s0223-5234(01)01225-9

  日期：2001.4

  A series of 1H-pyrazolo[3,4-d]pyrimidines (3-6) substituted at positions 1 (R-1 = Ph, H, tert-butyl and ribosetribenzoate), 4 (R-2 = chlorine, nitrogen and oxygen nucleophiles), and 6 (dimethylamino) have been synthesized and their effect on the release of histamine from rat peritoneal mast cells measured. After chemical stimulation, (polymer 48/80), several compounds (i.e. 3b, 4a, 4b, 4d, 4g, 5a), produce inhibition two to three times higher (40-60%) than DSCG but this action is lower after preincubation. 4b (R-1 = Ph, R-2 = NHCH2Ph; 50-70% inhibition) and 5a (R-1 = H, R-2 = OMe, 50-55% inhibition) are the most active ones in both experiments. With ovoalbumin as stimulus, several pyrazolopyrimidines show inhibition similar to DSCG, the most active compounds being 6a-d (IC50 = 12-16 muM; R-1 = ribosetribenzoate, R-2 = methoxy and amino), Compounds 4e (R-1 = t-butyl, R-2 = OMe) and 4g (R-1 = t-butyl, R-2 = piperidino) are inducers of the release of histamine (60 and 150% increase). Compounds 4b and 4e showed cytotoxic activity (IC50 =1 mug/ml) to HT-29 human colon cancer cells. (C) 2001 Editions scientifiques et medicales Elsevier SAS.