3-methyl-1-(2-methylpropyl)-6-(1-naphthylmethyl)pyrrolo<3,4-d>pyrimidine-2,4-dione | 166755-51-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-methyl-1-(2-methylpropyl)-6-(1-naphthylmethyl)pyrrolo<3,4-d>pyrimidine-2,4-dione
• 英文别名: 1-isobutyl-3-methyl-6-(naphthalen-1-ylmethyl)-1,6-dihydro-2H-pyrrolo[3,4-d]pyrimidine-2,4(3H)-dione；3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione；3-methyl-1-(2-methylpropyl)-6-(naphthalen-1-ylmethyl)pyrrolo[3,4-d]pyrimidine-2,4-dione
• CAS: 166755-51-7
• 化学式: C₂₂H₂₃N₃O₂
• 分子量: 361.444
• InChiKey: HSGYYWSMLDCHQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-1-(2-methylpropyl)-6-(1-naphthylmethyl)pyrrolo<3,4-d>pyrimidine-2,4-dione 生成 5-([4-methoxyphenyl]thio)-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione
  参考文献：
  名称：

  Pyrrolo[3,4-D] pyrimidinone derivatives and their use as medicaments

  摘要：

  该发明提供了一些新型的5-取代吡咯并[3,4-d]嘧啶-2,4-二酮，其制备方法，含有它们的药物组合物，制备药物组合物的方法，以及涉及其使用的治疗方法。

  公开号：

  US06046204A1
• 作为产物：
  描述：

  5-cyano-3,6-dimethyl-1-(2-methylpropyl)pyrimidine-2,4-dione 在 RaNi 甲酸 、 TEA 、 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 1.25h， 生成 3-methyl-1-(2-methylpropyl)-6-(1-naphthylmethyl)pyrrolo<3,4-d>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&lsqb;3,4-d&rsqb;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：AstraZeneca UK Limited

  公开号：US06136974A1

  公开（公告）日：2000-10-24

  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，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其使用的治疗方法。
• PYRROLO[3,4-d]PYRIMIDINONE DERIVATIVES AND THEIR USE AS IMMUNOSUPPRESSANTS
  申请人：AstraZeneca AB

  公开号：EP0946562B1

  公开（公告）日：2002-03-27