2-Bis[amino(methyl)amino]phosphoryloxyethyl 4-azido-2,3,5,6-tetrafluorobenzoate | 197070-57-8

• 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: 2-Bis[amino(methyl)amino]phosphoryloxyethyl 4-azido-2,3,5,6-tetrafluorobenzoate
• CAS: 197070-57-8
• 化学式: C₁₁H₁₄F₄N₇O₄P
• 分子量: 415.244
• InChiKey: SRYRMHGXEAZOPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  赖诺普利 、 2-Bis[amino(methyl)amino]phosphoryloxyethyl 4-azido-2,3,5,6-tetrafluorobenzoate 以 氘代甲醇 为溶剂， 生成
  参考文献：
  名称：

  Chemistry of Bifunctional Photoprobes

  摘要：

  The synthesis and biological activity of functionalized lisinopril, a potent angiotensin converting enzyme (ACE) inhibitor is described. Selective functionalization of lisinopril is achieved at the secondary amino position by a photochemical method, whereas esterfication of the carboxylic groups and modification at the primary amino group is achieved by chemical methods. Autoradiographic investigations using competitive I-125 radioactive binding assays with the modified lisinopril reveal that the terminal amino group modification enhanced the binding to ACE, whereas the secondary amino group functionalization did not differ significantly from the binding properties of native lisinopril. However, esterification of the carboxyl groups reduced the inhibitory potentency from nM to mu M. These results suggest that lisinopril can be derivatized with preservation of inhibition potency toward ACE. These modifications may find utility in the development of photoaffinity labeling agents for ACE or to incorporate bifunctional chelating agents carrying diagnostic radiometals for the development of cardiac imaging agents. (C) 1997 Academic Press.

  DOI：

  10.1006/bioo.1997.1055
• 作为产物：
  描述：

  五氟苯甲酰氯 在 sodium azide 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 氯仿 、 水 、 丙酮 为溶剂， 反应 16.0h， 生成 2-Bis[amino(methyl)amino]phosphoryloxyethyl 4-azido-2,3,5,6-tetrafluorobenzoate
  参考文献：
  名称：

  Chemistry of Bifunctional Photoprobes.¹ 3. Correlation between the Efficiency of CH Insertion by Photolabile Chelating Agents and Lifetimes of Singlet Nitrenes by Flash Photolysis:  First Example of Photochemical Attachment of ^99mTc−Complex with Human Serum Albumin

  摘要：

  Systematic functionalization of perfluoroaryl azides with chelating agents capable of complexing transition metals produces a new class of bifunctional photolabile chelating agents (BFPCAs). The strategy to shield the azide functionality from the electronic and steric influence of the electron-rich metal Pd through ester and amide bridges raised CH insertion efficiency to unprecedented levels (>92%) in a model solvent (cyclohexane). In contrast, perfluoroaryl azides attached to chelating agents via hydrazones show no significant CH insertion in cyclohexane upon photolysis. Measurements of the lifetimes of the singlet nitrenes derived from these agents by flash photolysis techniques correlate well with the efficiency of CH insertion by demonstrating longer lifetimes (10-50 times) for singlet nitrenes derived from azidotetrafluorinated esters and amides compared with the related hydrazones, which failed to yield significant CH insertion. A representative BFPCA 12 is chelated to diagnostic radionuclide Tc-94m and covalently attached to human serum albumin via photochemical activation extending the favorable bimolecular insertion characteristics of BFPCA to tracer level concentrations in buffer conditions. Flash photolysis experiments correlate singlet nitrene lifetimes with the efficiency of intermolecular insertion reactions. This work provides new photo-cross-linking technology, useful in radiodiagnostics and radiotherapy in nuclear medicine.

  DOI：

  10.1021/jo981458a

文献信息

• Chemistry of Bifunctional Photoprobes.¹ 3. Correlation between the Efficiency of CH Insertion by Photolabile Chelating Agents and Lifetimes of Singlet Nitrenes by Flash Photolysis:  First Example of Photochemical Attachment of ^99mTc−Complex with Human Serum Albumin
  作者：Raghoottama S. Pandurangi、Przemyslaw Lusiak、Robert R. Kuntz、Wynn A. Volkert、Jacek Rogowski、Matthew S. Platz

  DOI：10.1021/jo981458a

  日期：1998.11.1

  Systematic functionalization of perfluoroaryl azides with chelating agents capable of complexing transition metals produces a new class of bifunctional photolabile chelating agents (BFPCAs). The strategy to shield the azide functionality from the electronic and steric influence of the electron-rich metal Pd through ester and amide bridges raised CH insertion efficiency to unprecedented levels (>92%) in a model solvent (cyclohexane). In contrast, perfluoroaryl azides attached to chelating agents via hydrazones show no significant CH insertion in cyclohexane upon photolysis. Measurements of the lifetimes of the singlet nitrenes derived from these agents by flash photolysis techniques correlate well with the efficiency of CH insertion by demonstrating longer lifetimes (10-50 times) for singlet nitrenes derived from azidotetrafluorinated esters and amides compared with the related hydrazones, which failed to yield significant CH insertion. A representative BFPCA 12 is chelated to diagnostic radionuclide Tc-94m and covalently attached to human serum albumin via photochemical activation extending the favorable bimolecular insertion characteristics of BFPCA to tracer level concentrations in buffer conditions. Flash photolysis experiments correlate singlet nitrene lifetimes with the efficiency of intermolecular insertion reactions. This work provides new photo-cross-linking technology, useful in radiodiagnostics and radiotherapy in nuclear medicine.
• Chemistry of Bifunctional Photoprobes
  作者：Raghoottama S. Pandurangi、Przemyslaw Lusiak、Robert R. Kuntz、Yao Sun、Karl T. Weber

  DOI：10.1006/bioo.1997.1055

  日期：1997.4

  The synthesis and biological activity of functionalized lisinopril, a potent angiotensin converting enzyme (ACE) inhibitor is described. Selective functionalization of lisinopril is achieved at the secondary amino position by a photochemical method, whereas esterfication of the carboxylic groups and modification at the primary amino group is achieved by chemical methods. Autoradiographic investigations using competitive I-125 radioactive binding assays with the modified lisinopril reveal that the terminal amino group modification enhanced the binding to ACE, whereas the secondary amino group functionalization did not differ significantly from the binding properties of native lisinopril. However, esterification of the carboxyl groups reduced the inhibitory potentency from nM to mu M. These results suggest that lisinopril can be derivatized with preservation of inhibition potency toward ACE. These modifications may find utility in the development of photoaffinity labeling agents for ACE or to incorporate bifunctional chelating agents carrying diagnostic radiometals for the development of cardiac imaging agents. (C) 1997 Academic Press.