3,6-dimethyl-5-formyl-1-(1-methylethyl)pyrimidine-2,4-dione | 166755-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3,6-dimethyl-5-formyl-1-(1-methylethyl)pyrimidine-2,4-dione
• 英文别名: 1,4-dimethyl-2,6-dioxo-3-propan-2-ylpyrimidine-5-carbaldehyde
• CAS: 166755-05-1
• 化学式: C₁₀H₁₄N₂O₃
• 分子量: 210.233
• InChiKey: XRUKENKIBKOKFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,6-dimethyl-5-formyl-1-(1-methylethyl)pyrimidine-2,4-dione 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 6-Bromomethyl-1-isopropyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
  参考文献：
  名称：

  Novel Inhibitors of the Nuclear Factor of Activated T Cells (NFAT)-Mediated Transcription of .beta.-Galactosidase: Potential Immunosuppressive and Antiinflammatory Agents

  摘要：

  The preparation of a series of quinazoline-2,4-diones, 1-3, and pyrrolo[3,4-d]pyrimidine-2,4-diones, 4-8 is described. A small number of quinazolinedione analogs were identified from random screening to possess low micromolar (1.3-4.4 mu M) potency in the nuclear factor of activated T cells-1-regulated beta-galactosidase expression assay. An expanded analog search resulted in identifying pyrrolopyrimidinedione 4b which is 5-10-fold (0.26 mu M) more potent than the quinazolinediones. Replacement of the benzyl group with naphthyl led to greater potency and conformationally restricted analogs 4u-w. The naphthyl and acenaphthyl analogs are 10-100 times more potent inhibitors of beta-galactosidase expression than 4b. Binding affinity data for displacement of radiolabeled 4s from Jurkat cell membranes reflected an excellent correlation with the IC50 value for inhibition of beta-galactosidase activity. These products, whose structure-activity relationships are discussed, are of interest as potential agents for preventing interleukin-2 gene transcription.

  DOI：

  10.1021/jm00014a009
• 作为产物：
  描述：

  5-cyano-3,6-dimethyl-1-(1-methylethyl)pyrimidine-2,4-dione 在 RaNi 甲酸 作用下， 反应 0.25h， 生成 3,6-dimethyl-5-formyl-1-(1-methylethyl)pyrimidine-2,4-dione
  参考文献：
  名称：

  Novel Inhibitors of the Nuclear Factor of Activated T Cells (NFAT)-Mediated Transcription of .beta.-Galactosidase: Potential Immunosuppressive and Antiinflammatory Agents

  摘要：

  The preparation of a series of quinazoline-2,4-diones, 1-3, and pyrrolo[3,4-d]pyrimidine-2,4-diones, 4-8 is described. A small number of quinazolinedione analogs were identified from random screening to possess low micromolar (1.3-4.4 mu M) potency in the nuclear factor of activated T cells-1-regulated beta-galactosidase expression assay. An expanded analog search resulted in identifying pyrrolopyrimidinedione 4b which is 5-10-fold (0.26 mu M) more potent than the quinazolinediones. Replacement of the benzyl group with naphthyl led to greater potency and conformationally restricted analogs 4u-w. The naphthyl and acenaphthyl analogs are 10-100 times more potent inhibitors of beta-galactosidase expression than 4b. Binding affinity data for displacement of radiolabeled 4s from Jurkat cell membranes reflected an excellent correlation with the IC50 value for inhibition of beta-galactosidase activity. These products, whose structure-activity relationships are discussed, are of interest as potential agents for preventing interleukin-2 gene transcription.

  DOI：

  10.1021/jm00014a009

文献信息

• Pyrrolo[3,4-d]pyrimidinone derivatives and their use as medicaments
  申请人：AstraZeneca AB.

  公开号：US20020025966A1

  公开（公告）日：2002-02-28

  The invention provides certain novel 5-substituted pyrrolo[3,4-d]pyrimidine-2,4-diones, processes for their preparation, pharmaceutical compositions containing them, a process for preparing the pharmaceutical compositions, and methods of treatment involving their use.

  本发明提供了一些新颖的5-取代吡咯并[3,4-d]嘧啶-2,4-二酮，其制备方法，包含它们的制药组合物，制备制药组合物的方法以及使用它们进行治疗的方法。
• Pyrrolo(3,4-d)pyrimidinone derivatives and their use as medicaments
  申请人：AstraZeneca UK Limited

  公开号：US06211368B1

  公开（公告）日：2001-04-03

  Process for preparing 5-substituted pyrrolo [3,4-d] pyrimidine-2-4-diones of formula (I) wherein W, Q, R1, R2 and R10 are as defined in the specification and Y is COOH, wherein a corresponding C1-5 alkyl ester compound is hydrolyzed. The compounds are useful for treating or reducing the risk of reversible obstructive airways disease.

  制备5-取代吡咯并[3,4-d]嘧啶-2,4-二酮（式（I）中W、Q、R1、R2和R10定义如说明书，Y为COOH）的过程，其中相应的C1-5烷基酯化合物被水解。这些化合物可用于治疗或减少可逆性阻塞性呼吸道疾病的风险。
• Pyrrolo[3,4-d]pyrimidinone derivatives and their use as medicaments
  申请人：AstraZeneca UK Limited

  公开号：US06229013B1

  公开（公告）日：2001-05-08

  The invention provides certain novel 5-substituted pyrrolo[3,4-d]pyrimidine-2,4-diones, processes for their preparation, pharmaceutical compositions containing them, a process for preparing the pharmaceutical compositions, and methods of treatment involving their use.

  本发明提供了某些新型的5-取代吡咯并[3,4-d]嘧啶-2,4-二酮，以及它们的制备方法、包含它们的制药组合物、制备该制药组合物的方法以及涉及其使用的治疗方法。
• Pyrrolo[3,4-D] pyrimidinone derivatives and their use as medicaments
  申请人：Astra Pharmaceuticals Limited

  公开号：US06046204A1

  公开（公告）日：2000-04-04

  The invention provides certain novel 5-substituted pyrrolo[3,4-d]pyrimidine-2,4-diones, processes for their preparation, pharmaceutical compositions containing them, a process for preparing the pharmaceutical compositions, and methods of treatment involving their use.

  该发明提供了某些新型5-取代吡咯并[3,4-d]嘧啶-2,4-二酮，其制备方法，包含它们的制药组合物，制备制药组合物的方法以及涉及其使用的治疗方法。
• Pyrrolo[3,4-D]Pyrimidinone derivatives and their use as medicaments
  申请人：AstraZeneca UK Limited

  公开号：US06166206A1

  公开（公告）日：2000-12-26

  The invention provides certain novel 5-substituted pyrrolo[3,4-d]pyrimidine-2,4-diones, processes for their preparation, pharmaceutical compositions containing them, a process for preparing the pharmaceutical compositions, and methods of treatment involving their use.

  本发明提供了某些新型5-取代吡咯并[3,4-d]嘧啶-2,4-二酮，其制备方法，包含它们的制药组合物，制备该制药组合物的方法以及涉及使用它们的治疗方法。