4-methoxy-N,N-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine | 461670-52-0

• 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: 4-methoxy-N,N-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine
• CAS: 461670-52-0
• 化学式: C₈H₁₁N₅O
• 分子量: 193.208
• InChiKey: YOIBAWRUPZRSLQ-UHFFFAOYSA-N

物化性质

• 沸点：
  396.3±45.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-乙酰基-三-苄氧基-罗伯糖 、 4-methoxy-N,N-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine 在 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以50%的产率得到1-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-6-dimethylamino-4-methoxy-1H-pyrazolo[3,4-d]pyrimidine
  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：

  1-tert-butyl-4-methoxy-N,N-dimethylpyrazolo[3,4-d]pyrimidin-6-amine 在 甲酸 作用下， 以70%的产率得到4-methoxy-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

文献信息

• [EN] DIHYDROPYRAZOLOPYRIMIDINONE COMPOUNDS AS PDE2 INHIBITORS<br/>[FR] COMPOSÉS DIHYDROPYRAZOLOPYRIMIDINONE UTILISÉS EN TANT QU'EN TANT QU'INHIBITEURS DE PDE2
  申请人：MERCK SHARP & DOHME

  公开号：WO2016192083A1

  公开（公告）日：2016-12-08

  The present invention is directed to dihydropyrazolopyrimidinonecompounds of formula (I) which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

  本发明涉及式(I)的二氢吡唑并嘧啶酮化合物，该化合物作为治疗与磷酸二酯酶2 (PDE2)相关的中枢神经系统障碍的治疗剂是有用的。本发明还涉及使用这些化合物来治疗神经和精神障碍，如精神分裂症、精神病、帕金森病、帕金森病痴呆（PDD）或亨廷顿病，以及与纹状体功能减退或基底神经节功能障碍相关的疾病。