8-(3-bromopropylamino)-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione | 1276683-36-3

• 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: 8-(3-bromopropylamino)-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione
• 英文别名: 8-(3-bromopropylamino)-1,3,7-trimethylpurine-2,6-dione
• CAS: 1276683-36-3
• 化学式: C₁₁H₁₆BrN₅O₂
• 分子量: 330.184
• InChiKey: OSTAQUCYPRXQJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二苯甲基哌嗪 、 8-(3-bromopropylamino)-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以55%的产率得到1-benzhydryl-4-[1,3,7-trimethyl-2,6(3H,7H)-dioxo-1H-purine-8-aminopropyl]piperazine
  参考文献：
  名称：

  Synthesis, 5-HT1A and 5-HT2A receptor affinity and QSAR study of 1-benzhydryl-piperazine derivatives with xanthine moiety at N4

  摘要：

  Three novel 1-benzhydryl-piperazines with xanthine moiety at N4 were synthesized and tested for 5-HT1A and 5-HT2A receptor affinity. One of the compounds showed the highest affinity (58.6 nM) and selectivity (34 times) to 5-HT2A receptor known for this class of compounds. A set of the three new and 31 previously synthesized 1-arylpiperazines with xanthine moiety at N4 was compiled and a QSAR study was performed in order to rationalize the further synthesis. It was found that the 5-HT1A affinity depends on the shape of the molecules (ovality and number of circuits), the distribution of the electron density in the structures (partial charges at piperazine N1 and xanthine N1) and their charge transfer ability (HOMO energy). The 5-HT2A affinity depends on the lipophilicity of the ligands and the distribution of the electron density in the structures (partial charges at piperazine N4 and xanthine O6). The QSAR results are in a good agreement with known pharmacophore models.

  DOI：

  10.1007/s00044-011-9555-y
• 作为产物：
  描述：

  8-(3-Hydroxy-propylamino)-coffein 生成 8-(3-bromopropylamino)-1,3,7-trimethyl-1H-purine-2,6(3H,7H)-dione
  参考文献：
  名称：

  PEJKOV, PL.;ZLATKOV, AL.;GAGAUZOV, I.;KALINKOVA, G., FARMATSIYA, 40,(1990) N, S. 1-6

  摘要：

  DOI：