ethyl 2-(7-formyl-3H-imidazo[2,1-i]purin-3-yl)acetate | 1147498-01-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(7-formyl-3H-imidazo[2,1-i]purin-3-yl)acetate
• 英文别名: Ethyl 2-(7-formylimidazo[2,1-f]purin-3-yl)acetate
• CAS: 1147498-01-8
• 化学式: C₁₂H₁₁N₅O₃
• 分子量: 273.251
• InChiKey: YGCDBIIYQNAZPO-UHFFFAOYSA-N

物化性质

• 密度：
  1.55±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(7-formyl-3H-imidazo[2,1-i]purin-3-yl)acetate 在 盐酸 、 水 作用下， 以100%的产率得到2-[5-amino-4-(5-formyl-1H-imidazol-2-yl)imidazol-1-yl]acetic acid;hydrochloride
  参考文献：
  名称：

  Solid-Phase Synthesis of 4(5),1′,5′-Trisubstituted 2,4′-Biimidazoles

  摘要：

  A method for the synthesis of libraries of 4(5), 1',5'-tri substituted 2,4'-biimidazoles on a solid support was developed.(1) A trivalent scaffold, 2-(5'-amino-4(5)-formyl-1H,1'H-2,4'-biimidazol-1'-yl)acetic acid, was first prepared in solution by a two-step synthesis from ethyl adenin-9-ylacetate and bromomalonaldehyde. The product was coupled to an amino acid loaded Wang resin and the formyl group was subsequently derivatized either by reductive amination, oximation, or hydrazone formation. The 5'-amino group of the resin-bound biimidazole was then acylated and the products were finally released from the resin and purified. 5'-Amino-2,4'-biimidazole offers a scaffold for lead compounds of drug discovery, possibly useful in finding leads for protein kinase inhibitors.

  DOI：

  10.1021/jo902122e
• 作为产物：
  描述：

  6-乙基水杨酸甲酯 、 2-溴丙二醛 在 2,6-二甲基吡啶 、 甲酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以77%的产率得到ethyl 2-(7-formyl-3H-imidazo[2,1-i]purin-3-yl)acetate
  参考文献：
  名称：

  Solid-Phase Synthesis of 4(5),1′,5′-Trisubstituted 2,4′-Biimidazoles

  摘要：

  A method for the synthesis of libraries of 4(5), 1',5'-tri substituted 2,4'-biimidazoles on a solid support was developed.(1) A trivalent scaffold, 2-(5'-amino-4(5)-formyl-1H,1'H-2,4'-biimidazol-1'-yl)acetic acid, was first prepared in solution by a two-step synthesis from ethyl adenin-9-ylacetate and bromomalonaldehyde. The product was coupled to an amino acid loaded Wang resin and the formyl group was subsequently derivatized either by reductive amination, oximation, or hydrazone formation. The 5'-amino group of the resin-bound biimidazole was then acylated and the products were finally released from the resin and purified. 5'-Amino-2,4'-biimidazole offers a scaffold for lead compounds of drug discovery, possibly useful in finding leads for protein kinase inhibitors.

  DOI：

  10.1021/jo902122e

文献信息

• Solid-Phase Synthesis of 4(5),1′,5′-Trisubstituted 2,4′-Biimidazoles
  作者：Tuomas Karskela、Harri Lönnberg

  DOI：10.1021/jo902122e

  日期：2009.12.18

  A method for the synthesis of libraries of 4(5), 1',5'-tri substituted 2,4'-biimidazoles on a solid support was developed.(1) A trivalent scaffold, 2-(5'-amino-4(5)-formyl-1H,1'H-2,4'-biimidazol-1'-yl)acetic acid, was first prepared in solution by a two-step synthesis from ethyl adenin-9-ylacetate and bromomalonaldehyde. The product was coupled to an amino acid loaded Wang resin and the formyl group was subsequently derivatized either by reductive amination, oximation, or hydrazone formation. The 5'-amino group of the resin-bound biimidazole was then acylated and the products were finally released from the resin and purified. 5'-Amino-2,4'-biimidazole offers a scaffold for lead compounds of drug discovery, possibly useful in finding leads for protein kinase inhibitors.