1,3-dimethyl-2,4-dioxo-7-phenoxymethyl-1,2,3,4,6,7-hexahydrooxazolido<2,3-f>purine | 78960-54-0

• 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-2,4-dioxo-7-phenoxymethyl-1,2,3,4,6,7-hexahydrooxazolido<2,3-f>purine
• 英文别名: 1,3-Dimethyl-7-phenoxymethyl-6,7-dihydro-1H-oxazolo[2,3-f]purine-2,4-dione；2,4-dimethyl-7-(phenoxymethyl)-7,8-dihydropurino[8,7-b][1,3]oxazole-1,3-dione
• CAS: 78960-54-0
• 化学式: C₁₆H₁₆N₄O₄
• 分子量: 328.327
• InChiKey: ZSPWCBRZWTYFNO-UHFFFAOYSA-N

物化性质

• 熔点：
  181-182 °C(Solv: ethanol (64-17-5))
• 沸点：
  540.8±60.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)
• 溶解度：
  >49.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-2,4-dioxo-7-phenoxymethyl-1,2,3,4,6,7-hexahydrooxazolido<2,3-f>purine 、 C.I.酸性橙108 以59%的产率得到
  参考文献：
  名称：

  KREMZER, A. A.;STROKIN, YU. V.;SAMURA, B. A.;STEBLYUK, P. N., XIM.-FARMATS. ZH., 1981, 15, N 6, 59-64

  摘要：

  DOI：
• 作为产物：
  描述：

  8-溴茶碱 、 苯基缩水甘油醚 在 吡啶 作用下， 以 丙醇 为溶剂， 反应 2.0h， 以78%的产率得到1,3-dimethyl-2,4-dioxo-7-phenoxymethyl-1,2,3,4,6,7-hexahydrooxazolido<2,3-f>purine
  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

文献信息

• Reaction between 8-chlorotheophylline and epoxides. A simple preparation of oxazolido[2,3-f]purines
  作者：Ren-Hua Jin、Tadatomi Nishikubo

  DOI：10.1016/s0040-4039(00)60959-0

  日期：1992.10

  The reaction of epoxides with 8-chlorotheophylline () produced the corresponding oxazolido[2,3-f]purines via nucleophilic addition and intramolecular nucleophilc substitution

  环氧化物与8-氯茶碱（）的反应通过亲核加成和分子内亲核取代产生相应的恶唑醇[2,3-f]嘌呤
• Tricyclic oxazolo[2,3-f]purinediones: potency as adenosine receptor ligands and anticonvulsants
  作者：Anna Drabczyńska、Christa E. Müller、Britta Schumacher、Sonja Hinz、Janina Karolak-Wojciechowska、Barbara Michalak、Elżbieta Pękala、Katarzyna Kieć-Kononowicz

  DOI：10.1016/j.bmc.2004.06.043

  日期：2004.9

  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.
• KREMZER, A. A.;STROKIN, YU. V.;SAMURA, B. A.;STEBLYUK, P. N., XIM.-FARMATS. ZH., 1981, 15, N 6, 59-64
  作者：KREMZER, A. A.、STROKIN, YU. V.、SAMURA, B. A.、STEBLYUK, P. N.

  DOI：——

  日期：——