(E)-2-styryl-3H-imidazo[4,5-c]pyridin-4(5H)-one | 1419403-37-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: (E)-2-styryl-3H-imidazo[4,5-c]pyridin-4(5H)-one
• CAS: 1419403-37-4
• 化学式: C₁₄H₁₁N₃O
• 分子量: 237.261
• InChiKey: UZTFZVQAXJGQJC-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.54
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-2-styryl-3H-imidazo[4,5-c]pyridin-4(5H)-one 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 以28%的产率得到3,5-dimethyl-2-[(E)-2-phenylethenyl]imidazo[4,5-c]pyridin-4-one
  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：

  肉桂酸 在 乙酸酐 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 (E)-2-styryl-3H-imidazo[4,5-c]pyridin-4(5H)-one
  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