N-(4-{[(2-amino-9H-purin-6-yl)oxy]methyl}benzyl)-4-(2,7-difluoro-3,6-dihydroxy-xanthen-9H-yl)-3-methylbenzamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-{[(2-amino-9H-purin-6-yl)oxy]methyl}benzyl)-4-(2,7-difluoro-3,6-dihydroxy-xanthen-9H-yl)-3-methylbenzamide
• 英文别名: N-[[4-[(2-amino-7H-purin-6-yl)oxymethyl]phenyl]methyl]-4-(2,7-difluoro-3-hydroxy-6-oxoxanthen-9-yl)-3-methylbenzamide
• 化学式: C₃₄H₂₄F₂N₆O₅
• 分子量: 634.599
• InChiKey: DNHFCSVKADTNFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  47
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  165
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  4-氟间苯二酚 在 氢氧化钾 、 甲烷磺酸 、 对甲苯磺酸 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 51.0h， 生成 N-(4-{[(2-amino-9H-purin-6-yl)oxy]methyl}benzyl)-4-(2,7-difluoro-3,6-dihydroxy-xanthen-9H-yl)-3-methylbenzamide
  参考文献：
  名称：

  A Concise Synthesis of the Pennsylvania Green Fluorophore and Labeling of Intracellular Targets with O⁶-Benzylguanine Derivatives

  摘要：

  We report improved syntheses of the Pennsylvania Green and 4-carboxy-Pennsylvania Green fluorophores; the latter compound was prepared from methyl 4-iodo-3-methylbenzoate in a three-pot process (32% overall yield). Chinese hamster ovary cells expressing O-6-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O-6-benzyiguanine (SNAP-Tag substrates). Analysis of living cells by confocal microscopy revealed that Pennsylvania Green derivatives exhibit substantially higher cell permeability than analogous Oregon Green-derived molecular probes.

  DOI：

  10.1021/ol7015093

文献信息

• A Concise Synthesis of the Pennsylvania Green Fluorophore and Labeling of Intracellular Targets with <i>O</i><i>⁶</i>-Benzylguanine Derivatives
  作者：Laurie F. Mottram、Ewa Maddox、Markus Schwab、Florent Beaufils、Blake R. Peterson

  DOI：10.1021/ol7015093

  日期：2007.9.1

  We report improved syntheses of the Pennsylvania Green and 4-carboxy-Pennsylvania Green fluorophores; the latter compound was prepared from methyl 4-iodo-3-methylbenzoate in a three-pot process (32% overall yield). Chinese hamster ovary cells expressing O-6-alkylguanine-DNA alkyltransferase fusion proteins were treated with Pennsylvania Green and Oregon Green linked to O-6-benzyiguanine (SNAP-Tag substrates). Analysis of living cells by confocal microscopy revealed that Pennsylvania Green derivatives exhibit substantially higher cell permeability than analogous Oregon Green-derived molecular probes.