6-[(2,4-Dimethylphenyl)methylamino]-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one

• 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: 6-[(2,4-Dimethylphenyl)methylamino]-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one
• 英文别名: 6-[(2,4-dimethylphenyl)methylamino]-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one
• 化学式: C₁₄H₁₅N₅O
• 分子量: 269.306
• InChiKey: DYQCGPXSFVNIHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6-氯-1,5-二氢-4H-吡唑并[3,4-d]嘧啶-4-酮 、 2,4-二甲基苄胺 以 乙二醇甲醚 、 水 为溶剂， 生成 6-[(2,4-Dimethylphenyl)methylamino]-1,5-dihydropyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Novel Pyrazolo[3,4-d]pyrimidine-Based Inhibitors of Staphlococcus aureus DNA Polymerase III:  Design, Synthesis, and Biological Evaluation

  摘要：

  6-Anilinopyrazolo [3,4-d] pyrimidin-4-ones are novel dGTP analogues that inhibit the replication-specific, enzyme DNA polymerase III (DNA pol III) of Staphlococcus aureus and other Gram-positive (Gr+) bacteria. To enhance the potential of these inhibitors as antimicrobial agents, a structure-activity relationship was developed involving substitutions at the 2, 4, and pyrazolo NH positions. All of the new inhibitors were tested for their ability to inhibit S. aureus DNA pol III and the growth of several other Gr+ bacteria in culture. 2-Anilino groups with small hydrophobic groups in the meta or para position enhanced both antipolymerase and antimicrobial activity. 2-Benzyl-substituted inhibitors were substantially less active. Substitution in the 4-position by oxygen gave the optimal activity, whereas substitution at the pyrazolo NH was not tolerated. These pyrazolo[3,4-d]pyrimidine derivatives represent a novel class of antimicrobials with promising activities against Gr+ bacteria.

  DOI：

  10.1021/jm020483c

文献信息

• Novel Pyrazolo[3,4-<i>d</i>]pyrimidine-Based Inhibitors of <i>Staphlococcus aureus</i> DNA Polymerase III:  Design, Synthesis, and Biological Evaluation
  作者：Amjad Ali、Gayle E. Taylor、Ken Ellsworth、Georgianna Harris、Ronald Painter、Lynn L. Silver、Katherine Young

  DOI：10.1021/jm020483c

  日期：2003.5.1

  6-Anilinopyrazolo [3,4-d] pyrimidin-4-ones are novel dGTP analogues that inhibit the replication-specific, enzyme DNA polymerase III (DNA pol III) of Staphlococcus aureus and other Gram-positive (Gr+) bacteria. To enhance the potential of these inhibitors as antimicrobial agents, a structure-activity relationship was developed involving substitutions at the 2, 4, and pyrazolo NH positions. All of the new inhibitors were tested for their ability to inhibit S. aureus DNA pol III and the growth of several other Gr+ bacteria in culture. 2-Anilino groups with small hydrophobic groups in the meta or para position enhanced both antipolymerase and antimicrobial activity. 2-Benzyl-substituted inhibitors were substantially less active. Substitution in the 4-position by oxygen gave the optimal activity, whereas substitution at the pyrazolo NH was not tolerated. These pyrazolo[3,4-d]pyrimidine derivatives represent a novel class of antimicrobials with promising activities against Gr+ bacteria.