[6-bromo-7-(methoxymethoxy)-2-oxochromen-3-yl]methyl N-[2-[[2,6-bis(hydroxymethyl)-4-methylphenoxy]carbonyl-methylamino]ethyl]-N-methylcarbamate | 1277190-55-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: [6-bromo-7-(methoxymethoxy)-2-oxochromen-3-yl]methyl N-[2-[[2,6-bis(hydroxymethyl)-4-methylphenoxy]carbonyl-methylamino]ethyl]-N-methylcarbamate
• CAS: 1277190-55-2
• 化学式: C₂₇H₃₁BrN₂O₁₀
• 分子量: 623.455
• InChiKey: GRCUEPHNEYLWDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [6-bromo-7-(methoxymethoxy)-2-oxochromen-3-yl]methyl N-[2-[[2,6-bis(hydroxymethyl)-4-methylphenoxy]carbonyl-methylamino]ethyl]-N-methylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以61%的产率得到(6-bromo-7-hydroxy-2-oxochromen-3-yl)methyl N-[2-[[2,6-bis(hydroxymethyl)-4-methylphenoxy]carbonyl-methylamino]ethyl]-N-methylcarbamate
  参考文献：
  名称：

  Low Power, Biologically Benign NIR Light Triggers Polymer Disassembly

  摘要：

  Near infrared (NIR) irradiation can penetrate up to 10 cm deep into tissues and be remotely applied with high spatial and temporal precision. Despite its potential for various medical and biological applications, there is a dearth of biomaterials that are responsive at this wavelength region. Herein we report a polymeric material that is able to disassemble in response to biologically benign levels of NIR. irradiation upon two-photon absorption. The design relies on the photolysis of the multiple pendant 4-bromo7-hydroxycoumarin protecting groups to trigger a cascade of cyclization and rearrangement reactions leading to the degradation of the polymer backbone. The new material undergoes a 50% M-w loss after 25 s of ultraviolet (UV) irradiation by single photon absorption and 21 mm of NIR irradiation via two-photon absorption. Most importantly, even NIR irradiation at a biologically benign laser power is sufficient to cause significant polymer disassembly. Furthermore, this material is well tolerated by cells both before and after degradation. These results demonstrate for the first time a NIR sensitive material with potential to be used for in vivo applications.

  DOI：

  10.1021/ma201850q
• 作为产物：
  描述：

  2,6-bis(((tert-butyldimethylsilyl)oxy)methyl)-4-methylphenol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 [6-bromo-7-(methoxymethoxy)-2-oxochromen-3-yl]methyl N-[2-[[2,6-bis(hydroxymethyl)-4-methylphenoxy]carbonyl-methylamino]ethyl]-N-methylcarbamate
  参考文献：
  名称：

  Low Power, Biologically Benign NIR Light Triggers Polymer Disassembly

  摘要：

  Near infrared (NIR) irradiation can penetrate up to 10 cm deep into tissues and be remotely applied with high spatial and temporal precision. Despite its potential for various medical and biological applications, there is a dearth of biomaterials that are responsive at this wavelength region. Herein we report a polymeric material that is able to disassemble in response to biologically benign levels of NIR. irradiation upon two-photon absorption. The design relies on the photolysis of the multiple pendant 4-bromo7-hydroxycoumarin protecting groups to trigger a cascade of cyclization and rearrangement reactions leading to the degradation of the polymer backbone. The new material undergoes a 50% M-w loss after 25 s of ultraviolet (UV) irradiation by single photon absorption and 21 mm of NIR irradiation via two-photon absorption. Most importantly, even NIR irradiation at a biologically benign laser power is sufficient to cause significant polymer disassembly. Furthermore, this material is well tolerated by cells both before and after degradation. These results demonstrate for the first time a NIR sensitive material with potential to be used for in vivo applications.

  DOI：

  10.1021/ma201850q

文献信息

• Low Power, Biologically Benign NIR Light Triggers Polymer Disassembly
  作者：Nadezda Fomina、Cathryn L. McFearin、Marleen Sermsakdi、José M. Morachis、Adah Almutairi

  DOI：10.1021/ma201850q

  日期：2011.11.8

  Near infrared (NIR) irradiation can penetrate up to 10 cm deep into tissues and be remotely applied with high spatial and temporal precision. Despite its potential for various medical and biological applications, there is a dearth of biomaterials that are responsive at this wavelength region. Herein we report a polymeric material that is able to disassemble in response to biologically benign levels of NIR. irradiation upon two-photon absorption. The design relies on the photolysis of the multiple pendant 4-bromo7-hydroxycoumarin protecting groups to trigger a cascade of cyclization and rearrangement reactions leading to the degradation of the polymer backbone. The new material undergoes a 50% M-w loss after 25 s of ultraviolet (UV) irradiation by single photon absorption and 21 mm of NIR irradiation via two-photon absorption. Most importantly, even NIR irradiation at a biologically benign laser power is sufficient to cause significant polymer disassembly. Furthermore, this material is well tolerated by cells both before and after degradation. These results demonstrate for the first time a NIR sensitive material with potential to be used for in vivo applications.