ethyl 3-amino-5-(benzyloxy)-1H-indole-2-carboxylate | 1419403-52-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 3-amino-5-(benzyloxy)-1H-indole-2-carboxylate
• 英文别名: ethyl 3-amino-5-phenylmethoxy-1H-indole-2-carboxylate
• CAS: 1419403-52-3
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: WJLRNECWXMWKAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-5-(benzyloxy)-1H-indole-2-carboxylate 以 对二甲苯 、 异丙醇 为溶剂， 反应 48.0h， 生成 8-(benzyloxy)-3-methyl-1H-pyrimido[5,4-b]indole-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
• 作为产物：
  描述：

  ethyl 5-(benzyloxy)-3-(phenyldiazenyl)-1H-indole-2-carboxylate 在 盐酸 、 tin 作用下， 以 水 、 异丙醇 为溶剂， 反应 2.0h， 以69%的产率得到ethyl 3-amino-5-(benzyloxy)-1H-indole-2-carboxylate
  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

文献信息

• Synthesis of (<i>E</i>)-8-(3-Chlorostyryl)caffeine Analogues Leading to 9-Deazaxanthine Derivatives as Dual A_2A Antagonists/MAO-B Inhibitors
  作者：Silvia Rivara、Giovanni Piersanti、Francesca Bartoccini、Giuseppe Diamantini、Daniele Pala、Teresa Riccioni、Maria Antonietta Stasi、Walter Cabri、Franco Borsini、Marco Mor、Giorgio Tarzia、Patrizia Minetti

  DOI：10.1021/jm301686s

  日期：2013.2.14

  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).