(4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-dimethyl-amine | 461670-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-dimethyl-amine
• 英文别名: 4-chloro-N,N-dimethyl-1-phenylpyrazolo[3,4-d]pyrimidin-6-amine
• CAS: 461670-34-8
• 化学式: C₁₃H₁₂ClN₅
• 分子量: 273.725
• InChiKey: VHZMVYQATADGMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-胡椒基哌嗪 、 (4-Chloro-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-dimethyl-amine 以 四氢呋喃 为溶剂， 以64%的产率得到[4-(4-Benzo[1,3]dioxol-5-ylmethyl-piperazin-1-yl)-1-phenyl-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
• 作为产物：
  描述：

  5-氨基-1-苯基吡唑-4-腈 在 盐酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 74.0h， 生成 (4-Chloro-1-phenyl-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

• 6-Dimethylamino 1H-Pyrazolo[3,4-d]pyrimidine derivatives as new inhibitors of inflammatory mediators in intact cells
  作者：José M Quintela、Carlos Peinador、Liliana González、Isabel Devesa、M.Luisa Ferrándiz、Maria J Alcaraz、Ricardo Riguera

  DOI：10.1016/s0968-0896(02)00562-x

  日期：2003.3

  The synthesis of 6-dimethylamino 1H-pyrazolo[3,4-d]pyrimidines substituted at positions 1 and 4, and their effects on murine macrophage and human neutrophil functions are described. Several compounds and especially 4b-6b are potent inhibitors of PGE(2) generation in murine macrophages. This action is related to a direct effect on COX-2 activity without affecting the enzyme expression. Some of these compounds also inhibited COX-1 and COX-2 in human monocytes and 4b showed selectivity for COX-2 inhibition. (C) 2003 Elsevier Science Ltd. All rights reserved.