7-(4-hydroxy-pentyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione | 50868-13-8

• 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: 7-(4-hydroxy-pentyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione
• 英文别名: 7-(4-Hydroxypentyl)-1,3-dimethylpurine-2,6-dione
• CAS: 50868-13-8
• 化学式: C₁₂H₁₈N₄O₃
• 分子量: 266.3
• InChiKey: VBWKPDAEPJUUMO-UHFFFAOYSA-N

物化性质

• 沸点：
  499.1±51.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  78.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-二甲基-7-(4-氧代戊基)-3,7-二氢-嘌呤-2,6-二酮 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 7-(4-hydroxy-pentyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione
  参考文献：
  名称：

  Potentiation of cADPR-Induced Ca²⁺-Release by Methylxanthine Analogues

  摘要：

  Caffeine and other methylxanthines are known to induce Ca2+-release from intracellular stores via the ryanodine receptor. In the present work, a range of caffeine analogues, in which methyl groups at the 1 and 7 positions were replaced with alkyl chains containing different functional groups (oxo, hydroxyl, propargyl, ester, and acids), were synthesized. These compounds were then screened for their ability to potentiate Ca2+-release induced by cADPR (an endogenous modulator of ryanodine receptors) in sea urchin egg homogenates. Two of the synthesized methylxanthines, 1,3-dimethyl-7-(7-hydroxyoctyl)xanthine (37) and 3-methyl-7-(7-oxooctyl)-1-propargylxanthine (66), were shown to be more potent than caffeine in potentiating cADPR-induced Ca2+-release, while 1,3-dimethyl-7-(5-ethylcarboxypentyl)xanthine (14) was shown to be more efficacious. The development of new methylxanthine analogues may lead to a better understanding of ryanodine receptor function and could possibly provide novel therapeutic agents.

  DOI：

  10.1021/jm980469t

文献信息

• US4189469A
  申请人：——

  公开号：US4189469A

  公开（公告）日：1980-02-19
• US4515795A
  申请人：——

  公开号：US4515795A

  公开（公告）日：1985-05-07
• US4576947A
  申请人：——

  公开号：US4576947A

  公开（公告）日：1986-03-18
• Potentiation of cADPR-Induced Ca²⁺-Release by Methylxanthine Analogues
  作者：Rosaria A. Cavallaro、Luigi Filocamo、Annamaria Galuppi、Antony Galione、Mario Brufani、Armando A. Genazzani

  DOI：10.1021/jm980469t

  日期：1999.7.1

  Caffeine and other methylxanthines are known to induce Ca2+-release from intracellular stores via the ryanodine receptor. In the present work, a range of caffeine analogues, in which methyl groups at the 1 and 7 positions were replaced with alkyl chains containing different functional groups (oxo, hydroxyl, propargyl, ester, and acids), were synthesized. These compounds were then screened for their ability to potentiate Ca2+-release induced by cADPR (an endogenous modulator of ryanodine receptors) in sea urchin egg homogenates. Two of the synthesized methylxanthines, 1,3-dimethyl-7-(7-hydroxyoctyl)xanthine (37) and 3-methyl-7-(7-oxooctyl)-1-propargylxanthine (66), were shown to be more potent than caffeine in potentiating cADPR-induced Ca2+-release, while 1,3-dimethyl-7-(5-ethylcarboxypentyl)xanthine (14) was shown to be more efficacious. The development of new methylxanthine analogues may lead to a better understanding of ryanodine receptor function and could possibly provide novel therapeutic agents.