3,9-dihydro-3-[(2-hydroxyethoxy)methyl]-6-(4-nitrophenyl)-9-oxo-5H-imidazo[1,2-a]purine | 381232-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,9-dihydro-3-[(2-hydroxyethoxy)methyl]-6-(4-nitrophenyl)-9-oxo-5H-imidazo[1,2-a]purine
• 英文别名: 3-(2-hydroxyethoxymethyl)-6-(4-nitrophenyl)-5H-imidazo[1,2-a]purin-9-one
• CAS: 381232-89-9
• 化学式: C₁₆H₁₄N₆O₅
• 分子量: 370.324
• InChiKey: JFXHXZUGXOSMCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,9-dihydro-3-[(2-hydroxyethoxy)methyl]-6-(4-nitrophenyl)-9-oxo-5H-imidazo[1,2-a]purine 在 palladium on activated charcoal 吡啶 、 ammonium formate 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 3-[(2-acetyloxyethoxy)methyl]-6-(4-aminophenyl)-3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine
  参考文献：
  名称：

  Synthesis and Biological Activity of Strongly Fluorescent Tricyclic Analogues of Acyclovir and Ganciclovir

  摘要：

  In search of strongly fluorescent tricyclic analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2), derivatives of the 3,9-dihydro-9-oxo-5H-imidazo[1,2-alpha]purine system, several 6-[4-(acyloxy)phenyl], 6- [4-(acylamino)phenyl], and 6- [4-(phenoxycarbonyloxy)phenyl]-substituted TACV and TGCV analogues were synthesized and evaluated for their activity against herpes simplex virus types 1 and 2 in cell culture. All TACV and TGCV analogues showed strong fluorescence (quantum yield of 30-65% vs 2-aminopurine 100%). The 6-[4-(phenoxycarbonyloxy)phenyl]-substituted compounds 11 and 19 displayed the best combination of the fluorescence and antiviral potency.

  DOI：

  10.1021/jm020827z
• 作为产物：
  描述：

  阿昔洛韦 在 ammonium hydroxide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3,9-dihydro-3-[(2-hydroxyethoxy)methyl]-6-(4-nitrophenyl)-9-oxo-5H-imidazo[1,2-a]purine
  参考文献：
  名称：

  Fluorescent Tricyclic Analogues of Acyclovir and Ganciclovir. A Structure−Antiviral Activity Study

  摘要：

  Of a series of new guanine base modified tricyclic analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2), derivatives of the 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine system, evaluated for activity against herpes simplex virus type 1 and 2, several fluorescent analogues, 6-(4-MeOPli)-TACV (8), 7-Me-6-Ph-TACV (17), 6-(4-MeOPh)-TGCV (27), and 7-Me-6-Ph-TGCV (28), were obtained that showed similar potency and selectivity as the parent compounds. The activity was found to Le strongly dependent on the nature and steric demands of the substituents in the 6 and/or 7 position.

  DOI：

  10.1021/jm010922s

文献信息

• Synthesis and Biological Activity of Strongly Fluorescent Tricyclic Analogues of Acyclovir and Ganciclovir
  作者：Tomasz Goslinski、Bozenna Golankiewicz、Erik De Clercq、Jan Balzarini

  DOI：10.1021/jm020827z

  日期：2002.11.1

  In search of strongly fluorescent tricyclic analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2), derivatives of the 3,9-dihydro-9-oxo-5H-imidazo[1,2-alpha]purine system, several 6-[4-(acyloxy)phenyl], 6- [4-(acylamino)phenyl], and 6- [4-(phenoxycarbonyloxy)phenyl]-substituted TACV and TGCV analogues were synthesized and evaluated for their activity against herpes simplex virus types 1 and 2 in cell culture. All TACV and TGCV analogues showed strong fluorescence (quantum yield of 30-65% vs 2-aminopurine 100%). The 6-[4-(phenoxycarbonyloxy)phenyl]-substituted compounds 11 and 19 displayed the best combination of the fluorescence and antiviral potency.
• Fluorescent Tricyclic Analogues of Acyclovir and Ganciclovir. A Structure−Antiviral Activity Study
  作者：Bozenna Golankiewicz、Tomasz Ostrowski、Tomasz Goslinski、Piotr Januszczyk、Joanna Zeidler、Daniel Baranowski、Erik de Clercq

  DOI：10.1021/jm010922s

  日期：2001.11.1

  Of a series of new guanine base modified tricyclic analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2), derivatives of the 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine system, evaluated for activity against herpes simplex virus type 1 and 2, several fluorescent analogues, 6-(4-MeOPli)-TACV (8), 7-Me-6-Ph-TACV (17), 6-(4-MeOPh)-TGCV (27), and 7-Me-6-Ph-TGCV (28), were obtained that showed similar potency and selectivity as the parent compounds. The activity was found to Le strongly dependent on the nature and steric demands of the substituents in the 6 and/or 7 position.