6-iodo-1,3,5-trimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione | 1419403-90-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 6-iodo-1,3,5-trimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione
• 英文别名: 6-Iodo-1,3,5-trimethylpyrrolo[3,2-d]pyrimidine-2,4-dione
• CAS: 1419403-90-9
• 化学式: C₉H₁₀IN₃O₂
• 分子量: 319.102
• InChiKey: CKOHSEYZEIMIQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-iodo-1,3,5-trimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione 、 4-氯-3-(三氟甲基)苯甲醇 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以38%的产率得到6-[[4-Chloro-3-(trifluoromethyl)phenyl]methoxy]-1,3,5-trimethylpyrrolo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of (E)-8-(3-Chlorostyryl)caffeine Analogues Leading to 9-Deazaxanthine Derivatives as Dual A_2A Antagonists/MAO-B Inhibitors

  摘要：

  A systematic modification of the caffeinyl core and substituents of the reference compound (E)-8-(3-chlorostyryl)caffeine led to the 9-deazaxanthine derivative (E)-6-(4-chlorostyryl)-1,3,5,=trimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4-(3H,5H)-dione (17f), which acts as a dual human A(2a) antagonist/MAO-B inhibitor (K-i(A(2A)) = 260 nM; IC50(MAO-B) = 200 nM; IC50(MAO-A) = 10 mu M) and dose dependently counteracts haloperidol-induced catalepsy in mice from 30 mg/kg by the oral route. The compound is the best balanced A(2A) antagonist/MAO-B inhibitor reported to date, and it could be considered as a new lead in the field of anti-Parkinson's agents. A number of analogues of 17f were synthesized and qualitative SARs are discussed. Two analogues of 17f, namely 18b and 19a, inhibit MAO-B with IC50 of 68 and 48 nM, respectively, being 5-7-fold more potent than the prototypical MAO-B inhibitor deprenyl (IC50 = 334 nM).

  DOI：

  10.1021/jm301686s
• 作为产物：
  描述：

  6-bromo-1,3,5-trimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione 在 copper(l) iodide 、 potassium iodide 、 N,N'-二甲基乙二胺 作用下， 以 正丁醇 为溶剂， 反应 36.0h， 以72%的产率得到6-iodo-1,3,5-trimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione
  参考文献：
  名称：

  Synthesis of (E)-8-(3-Chlorostyryl)caffeine Analogues Leading to 9-Deazaxanthine Derivatives as Dual A_2A Antagonists/MAO-B Inhibitors

  摘要：

  A systematic modification of the caffeinyl core and substituents of the reference compound (E)-8-(3-chlorostyryl)caffeine led to the 9-deazaxanthine derivative (E)-6-(4-chlorostyryl)-1,3,5,=trimethyl-1H-pyrrolo[3,2-d]pyrimidine-2,4-(3H,5H)-dione (17f), which acts as a dual human A(2a) antagonist/MAO-B inhibitor (K-i(A(2A)) = 260 nM; IC50(MAO-B) = 200 nM; IC50(MAO-A) = 10 mu M) and dose dependently counteracts haloperidol-induced catalepsy in mice from 30 mg/kg by the oral route. The compound is the best balanced A(2A) antagonist/MAO-B inhibitor reported to date, and it could be considered as a new lead in the field of anti-Parkinson's agents. A number of analogues of 17f were synthesized and qualitative SARs are discussed. Two analogues of 17f, namely 18b and 19a, inhibit MAO-B with IC50 of 68 and 48 nM, respectively, being 5-7-fold more potent than the prototypical MAO-B inhibitor deprenyl (IC50 = 334 nM).

  DOI：

  10.1021/jm301686s