4-[(phenoxycarbonyl)amino]phenacyl bromide | 476360-60-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[(phenoxycarbonyl)amino]phenacyl bromide
• 英文别名: phenyl N-[4-(2-bromoacetyl)phenyl]carbamate
• CAS: 476360-60-8
• 化学式: C₁₅H₁₂BrNO₃
• 分子量: 334.169
• InChiKey: JFVWJPPKYQNWRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(phenoxycarbonyl)amino]phenacyl bromide 在 氨 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 [4-[3-(2-hydroxyethoxymethyl)-9-oxo-5H-imidazo[1,2-a]purin-6-yl]phenyl]urea
  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：

  氯甲酸苯酯 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-[(phenoxycarbonyl)amino]phenacyl 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 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.