1,3-Dimethyl-7-propyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione | 344455-29-4

• 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: 1,3-Dimethyl-7-propyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione
• CAS: 344455-29-4
• 化学式: C₁₂H₁₆N₄O₃
• 分子量: 264.284
• InChiKey: YDMQBIRUKOPFNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.01
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  71.05
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  dirhodium tetrakis[(R)-α-methoxy-α-(trifluoromethyl)-phenylacetate] 、 1,3-Dimethyl-7-propyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione 以 氘代氯仿 、 氘代丙酮 为溶剂， 生成
  参考文献：
  名称：

  Modes of Xanthine Complexation to Dirhodium Tetrakis[(R)-α-methoxy-α- (trifluoromethyl)-phenylacetate] in Solution and in the Solid State

  摘要：

  通过红外光谱和核磁共振研究表明，在溶液中黄嘌呤1-5更倾向于与手性二铑四[(R)-α-甲氧基-α-(三氟甲基)苯乙酸乙酯基] (Rh*)成侧面配位，而在固态中则涉及到羰基。对于6，至少羰基C-6在溶液中也有贡献于配位。通过详细描述的X射线衍射分析揭示，固态中存在6和Rh*的交替链。通过“二铑法”（在Rh*存在下进行的¹H和¹³C NMR）可以轻松确定手性黄嘌呤6的对映异构体过量。

  DOI：

  10.1515/znb-2001-0317
• 作为产物：
  描述：

  丙基环氧乙烷 、 8-溴茶碱 在 吡啶 作用下， 以 正丁醇 为溶剂， 反应 4.0h， 以91%的产率得到1,3-Dimethyl-7-propyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione
  参考文献：
  名称：

  Tricyclic oxazolo[2,3-f]purinediones: potency as adenosine receptor ligands and anticonvulsants

  摘要：

  Synthesis and physicochemical properties of 7-mono- and 6,7-disubstituted dihydrooxazolo-[3,2-f]purinediones are described. Oxazolo[2,3-f]purinediones were synthesized by cyclization of 8-bromotheophylline with oxiranes. The obtained compounds (1-22) were evaluated for their affinity at adenosine A(1) and A(2A) receptors. They showed mainly adenosine A(2A) receptor affinity at low micromolar concentrations and A(2A) selectivity, for example, compound 9 with an octyl substituent at the oxazole ring displayed adenosine A(2A) receptor affinity (K-i=0.998muM) and at least 25-fold A(2A) versus A(1) selectivity. This compound was less selective (5-fold) towards human recombinant A(2B) and A(3) adenosine receptors. In this group of compounds active adenosine A, receptor antagonists were also identified. Oxazolopurinediones were evaluated in vivo as anticonvulsants in MES and ScMet tests and examined for neurotoxicity in mice (ip). Compounds with long alkyl chains showed anticonvulsant activity in both tests (in 100 and 300mg/kg doses), accompanied by significant neurotoxicity. The anticonvulsant activity in rats (po) was higher and without signs of neurotoxicity. SAR and QSAR studies stressed the importance of lipophilic 7-substituents for both types of pharmacological activity. The volume of the substituent is, however, limited at the A(2A) AR, an n-octyl group being optimal. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.043