1-(1-benzoylethyl)-9-[(1,3-dihydroxy-2-propoxy)methyl]guanine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(1-benzoylethyl)-9-[(1,3-dihydroxy-2-propoxy)methyl]guanine
• 英文别名: 1-(1-benzoylethyl)-GCV；2-Amino-9-(1,3-dihydroxypropan-2-yloxymethyl)-1-(1-oxo-1-phenylpropan-2-yl)purin-6-one
• 化学式: C₁₈H₂₁N₅O₅
• 分子量: 387.395
• InChiKey: SMJUSMPVSDJNSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(1-benzoylethyl)-9-[(1,3-dihydroxy-2-propoxy)methyl]guanine 在 ammonium hydroxide 作用下， 以9%的产率得到3-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-7-methyl-6-phenyl-5H-imidazo[1,2-a]purin-9-one
  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
• 作为产物：
  描述：

  更昔洛韦 、 2-溴苯丙酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以19%的产率得到1-(1-benzoylethyl)-9-[(1,3-dihydroxy-2-propoxy)methyl]guanine
  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

• 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.