3',6'-di(trimethylacetyloxy)-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carbonyl azide | 1254577-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3',6'-di(trimethylacetyloxy)-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carbonyl azide
• CAS: 1254577-94-0
• 化学式: C₃₁H₂₇N₃O₈
• 分子量: 569.571
• InChiKey: ZITWXUGNINVQLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  42.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  153.96
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3',6'-di(trimethylacetyloxy)-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carbonyl azide 以 甲苯 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  A fluorescein-containing, small-molecule, water-soluble receptor for cytosine free bases

  摘要：

  In this study, we synthesized small-molecule, water-soluble, fluorescein-containing ureido compounds 6 and 8 as target receptors for cytosine free bases and then investigated the binding of cytosine free bases with the receptors using (15)N NMR spectroscopy and partially labeled cytosine-2,4-(13)C-1,3,4-(15)N-cytosine. Binding with the receptor 6a (the disodium form of 6) caused the chemical shift of the nitrogen atom of the amino group of cytosine to move downfield; binding of the receptor 8a (the disodium form of 8), which is possessing no corresponding aryl nitrogen atom, had no effect on this signal. Fluorescence spectroscopy revealed that binding of cytosine and its derivatives led to quenching of the fluorescence of receptor 6a; in contrast, the quenching of receptor 8a was only slightly affected by cytosine. Because the fluorescence of 6a was not quenched by either deoxycytidine or uracil, it appears that this receptor is a specific for cytosine among the DNA bases. We used the fluorescence of 6a to measure the apparent binding constants for various cytosine derivatives, including the anticancer prodrug 5-fluorocytosine. Receptor 6a is the first small-molecule, water-soluble fluorescent receptor for the specific binding of cytosine free bases in aqueous solution. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.013
• 作为产物：
  描述：

  6-羧基荧光素二硬脂酸酯N-羟基琥珀酰亚胺酯 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 3.5h， 以1.25 g的产率得到3',6'-di(trimethylacetyloxy)-3-oxospiro[isobenzofuran-1(3H),9'-[9H]xanthene]-6-carbonyl azide
  参考文献：
  名称：

  A fluorescein-containing, small-molecule, water-soluble receptor for cytosine free bases

  摘要：

  In this study, we synthesized small-molecule, water-soluble, fluorescein-containing ureido compounds 6 and 8 as target receptors for cytosine free bases and then investigated the binding of cytosine free bases with the receptors using (15)N NMR spectroscopy and partially labeled cytosine-2,4-(13)C-1,3,4-(15)N-cytosine. Binding with the receptor 6a (the disodium form of 6) caused the chemical shift of the nitrogen atom of the amino group of cytosine to move downfield; binding of the receptor 8a (the disodium form of 8), which is possessing no corresponding aryl nitrogen atom, had no effect on this signal. Fluorescence spectroscopy revealed that binding of cytosine and its derivatives led to quenching of the fluorescence of receptor 6a; in contrast, the quenching of receptor 8a was only slightly affected by cytosine. Because the fluorescence of 6a was not quenched by either deoxycytidine or uracil, it appears that this receptor is a specific for cytosine among the DNA bases. We used the fluorescence of 6a to measure the apparent binding constants for various cytosine derivatives, including the anticancer prodrug 5-fluorocytosine. Receptor 6a is the first small-molecule, water-soluble fluorescent receptor for the specific binding of cytosine free bases in aqueous solution. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.013