4-isobutyryloxyphenacyl bromide | 476360-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-isobutyryloxyphenacyl bromide
• 英文别名: Propanoic acid, 2-methyl-, 4-(bromoacetyl)phenyl ester；[4-(2-bromoacetyl)phenyl] 2-methylpropanoate
• CAS: 476360-57-3
• 化学式: C₁₂H₁₃BrO₃
• 分子量: 285.137
• InChiKey: PGEIIZDNZLQVAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  46-49 °C
• 沸点：
  357.6±22.0 °C(Predicted)
• 密度：
  1.389±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-isobutyryloxyphenacyl bromide 在 氨 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6-(4-hydroxyphenyl)-5H-imidazo[1,2-a]purin-9-one
  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：

  对羟基苯乙酮 在 吡啶 、 三氯化铝 、 溴 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 4-isobutyryloxyphenacyl bromide
  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).
• Synthesis of a technetium-99m labeled tricyclic ganciclovir analog for non-invasive reporter gene expression imaging
  作者：Yi Zhang、Jing Lin、Dongfeng Pan

  DOI：10.1016/j.bmcl.2006.10.077

  日期：2007.2

  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.
• 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.