1-(4-羟基戊基)-3,7-二甲基-1H-嘌呤-2,6-(2H,6H)-二酮 | 50868-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 1-(4-羟基戊基)-3,7-二甲基-1H-嘌呤-2,6-(2H,6H)-二酮
• 英文名称: 1-(4-hydroxypentyl)-3,7-dimethyl-1H-purine-2,6(2H,6H)-dione
• 英文别名: 1-(4-hydroxy-pentyl)-3,7-dimethyl-3,7-dihydro-purine-2,6-dione；1-(4-Hydroxypentyl)-3,7-dimethylpurine-2,6-dione
• CAS: 50868-10-5
• 化学式: C₁₂H₁₈N₄O₃
• 分子量: 266.3
• InChiKey: CYCCBWAHGKLLTR-UHFFFAOYSA-N

物化性质

• 沸点：
  505.2±56.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 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

• 作为反应物：
  描述：

  1-(4-羟基戊基)-3,7-二甲基-1H-嘌呤-2,6-(2H,6H)-二酮 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 5-氨基戊烷-2-醇
  参考文献：
  名称：

  Predictable Stereoselective and Chemoselective Hydroxylations and Epoxidations with P450 3A4

  摘要：

  Enantioselective hydroxylation of one specific methylene in the presence of many similar groups is debatably the most challenging chemical transformation. Although chemists have recently made progress toward the hydroxylation of inactivated C-H bonds, enzymes such as P450s (CYPs) remain unsurpassed in specificity and scope. The substrate promiscuity of many P450s is desirable for synthetic applications; however, the inability to predict the products of these enzymatic reactions is impeding advancement. We demonstrate here the utility of a chemical auxiliary to control the selectivity of CYP3A4 reactions. When linked to substrates, inexpensive, achiral theobromine directs the reaction to produce hydroxylation or epoxidation at the fourth carbon from the auxiliary with pro-R facial selectivity. This strategy provides a versatile yet controllable system for regio-, chemo-, and stereoselective oxidations at inactivated C-H bonds and demonstrates the utility of chemical auxiliaries to mediate the activity of highly promiscuous enzymes.

  DOI：

  10.1021/ja200551y
• 作为产物：
  描述：

  5-Tosyloxy-2,2-ethylenedioxypentane 在 盐酸 、 甲醇 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 生成 1-(4-羟基戊基)-3,7-二甲基-1H-嘌呤-2,6-(2H,6H)-二酮
  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

• US4364922A
  申请人：——

  公开号：US4364922A

  公开（公告）日：1982-12-21
• 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
• US5780476A
  申请人：——

  公开号：US5780476A

  公开（公告）日：1998-07-14
• US6133274A
  申请人：——

  公开号：US6133274A

  公开（公告）日：2000-10-17