[4-[3-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-9-oxo-5H-imidazo[1,2-a]purin-6-yl]phenyl] 2-methylpropanoate | 476360-70-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [4-[3-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-9-oxo-5H-imidazo[1,2-a]purin-6-yl]phenyl] 2-methylpropanoate
• 英文别名: [4-[3-(1,3-dihydroxypropan-2-yloxymethyl)-9-oxo-5H-imidazo[1,2-a]purin-6-yl]phenyl] 2-methylpropanoate
• CAS: 476360-70-0
• 化学式: C₂₁H₂₃N₅O₆
• 分子量: 441.444
• InChiKey: SGOJZMPTJKOFIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [4-[3-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-9-oxo-5H-imidazo[1,2-a]purin-6-yl]phenyl] 2-methylpropanoate 在 氨 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-(2,2-dimethyl-[1,3]dioxan-5-yloxymethyl)-6-(4-hydroxy-phenyl)-3,5-dihydro-1,3,4,5,7a-pentaaza-s-indacen-8-one
  参考文献：
  名称：

  Synthesis of a technetium-99m labeled tricyclic ganciclovir analog for non-invasive reporter gene expression imaging

  摘要：

  A potential radiopharmaceutical and HSV1-TK substrate, 3-((1,3-dihydroxypropan-2-yloxy)-methyl)-6-(4-(3-((2-mercaptoethyl)(2-(2-mercaptoethyl-amino)-ethyl)amino)propoxy)phenyl)-3H-imidazopurin-9(5H)-one-oxo-technetium(V), was synthesized via a converging approach and its chemical structure was comparatively characterized with a non-radioactive analog. The final radiochemical purity and yield were 97 and 73%, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.077
• 作为产物：
  描述：

  4-isobutyryloxyacetophenone 在 三氯化铝 、 溴 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 [4-[3-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-9-oxo-5H-imidazo[1,2-a]purin-6-yl]phenyl] 2-methylpropanoate
  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

文献信息

• Synthesis and Fluorescent Properties of 6-(4-Biphenylyl)-3,9-dihydro-9-oxo-5<i>H</i>-imidazo[1,2-<i>A</i>]purine Analogues of Acyclovir and Ganciclovir
  作者：Tomasz Goslinski、Grazyna Wenska、Bozenna Golankiewicz、Jan Balzarini、Erik De Clercq

  DOI：10.1081/ncn-120022684

  日期：2003.10

  Tricyclic (T) analogues of acyclovir (ACV, 1) and ganciclovir (GCV, 2) carrying the 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purine system [i.e., 6-(4-BrPh)TACV, 5 and 6-(4-BrPh)TGCV, 6] were transformed into 6-[(4'-R-2)-4-biphenylyl] derivatives of TACV (7-9) and TGCV (10-12) by Suzuki cross coupling with 4-substituted phenylboronic acids. Compound 11 (R-2 = CH2OH) showed a high (similar to1000) selectivity index against herpes simplex virus type 1 (HSV-1) together with advantageous fluorescence properties (emission in visible region, little overlap with absorption and moderate intensity).