6-Bromomethyl-1-isopropyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde | 1028306-86-6

• 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: 6-Bromomethyl-1-isopropyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
• 英文别名: 4-(Bromomethyl)-1-methyl-2,6-dioxo-3-propan-2-ylpyrimidine-5-carbaldehyde
• CAS: 1028306-86-6
• 化学式: C₁₀H₁₃BrN₂O₃
• 分子量: 289.129
• InChiKey: LKIXMCIIYHRTJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  3
• 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：

  1-萘甲基胺 、 6-Bromomethyl-1-isopropyl-3-methyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 在 TEA 作用下， 以 乙醇 为溶剂， 生成 3-methyl-1-(1-methylethyl)-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
• 作为产物：
  描述：

  5-cyano-3,6-dimethyl-1-(1-methylethyl)pyrimidine-2,4-dione 在 RaNi 甲酸 、 溴 作用下， 以 氯仿 为溶剂， 反应 1.25h， 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