5-methyl-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4,6-(5H,7H)-dione | 24543-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 5-methyl-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4,6-(5H,7H)-dione
• 英文别名: 4,6-Dioxo-5-methyl-1-phenyl-4,5,6,7-tetrahydro-pyrazolo<3,4-d>pyrimidin；5-methyl-1-phenyl-1,7-dihydro-pyrazolo[3,4-d]pyrimidine-4,6-dione；5-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione；5-methyl-1-phenyl-7H-pyrazolo[3,4-d]pyrimidine-4,6-dione
• CAS: 24543-03-1
• 化学式: C₁₂H₁₀N₄O₂
• mdl: MFCD03764174
• 分子量: 242.237
• InChiKey: GJXAWGNCRURSDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4,6-(5H,7H)-dione 、 碘甲烷 在 sodium hydride 作用下， 生成 5,7-dimethyl-1-phenyl-1,7-dihydro-pyrazolo[3,4-d]pyrimidine-4,6-dione 、 6-Methoxy-5-methyl-1-phenyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Conformationally restrained, chiral (phenylisopropyl)amino-substituted pyrazolo[3,4-d]pyrimidines and purines with selectivity for adenosine A1 and A2 receptors

  摘要：

  Two modes of tethering a chiral (phenylisopropyl)amino substituent in pyrazolo[3,4-d]pyrimidines and purines have been explored. One mode gave (S)-2,7-dihydro-7-phenyl-2-(phenylmethyl)-5-propoxy-3H-imidazo[1,2-c]pyrazolo-[4,3-e]pyrimidine (12a) and its corresponding R-enantiomer 12b, which were selective for A2 and A1 adenosine receptors, respectively. The corresponding diimidazo[1,2-c:4',5'-e]pyrimidines 12e and 12f were analogously selective. This is the first example where a single chiral recognition unit provides enantiomers with opposite selectivities for adenosine receptors. The second mode gave (2S-trans)-2,7-dihydro-2-methyl-3,7-diphenyl-5-propoxy-3H-imidazo[1,2-c]-pyrazolo[4,3-e]pyrimidine (12c) and its corresponding R-enantiomer 12d. Compounds 12c and 12d were significantly less potent than 12a and 12b at A1 receptors, and were nonselective.

  DOI：

  10.1021/jm00095a024
• 作为产物：
  描述：

  6-[furan-2-ylmethyl(methyl)amino]-3-methyl-2,4-dioxo-1H-pyrimidine-5-carbaldehyde 在 lead(IV) acetate 、 sodium acetate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.5h， 生成 5-methyl-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine-4,6-(5H,7H)-dione
  参考文献：
  名称：

  Studies on pyrimidine-annelated heterocycles: synthesis of novel pyrazolo[3′,4′:4,5]pyrido[2,3-d]pyrimidines by intramolecular 1,3-dipolar cycloadditions

  摘要：

  Suitably functionalised 1,3-substituted 6-chloro-1,2,3,4-tetrahydro-2,4-dioxopyrimidine-5-carbaldehydes 3a-1 cyclise intramolecularly to yield novel furo- and thieno-[2 '',3 '':4',5']pyrazolo[3',4':4,5]pyrido-[2,3-d]pyrimidines 8a-1 in fair to good yields together with the pyrazolopyrimidines 7 as side products. Remarkably, this synthesis not only left the pyrimidine nucleus unaffected but also gave no dimer formation.

  DOI：

  10.1039/p19960001999