(6R,7R,24R,25R)-6,7,24,25-tetramethoxy-6,7,24,25-tetramethyl-14,17,32,35-tetra(propan-2-yloxy)-5,8,23,26-tetraoxa-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,9,11,13,15,17,19(39),20,22(27),28,30(37),31,33,35-pentadecaene | 1215003-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (6R,7R,24R,25R)-6,7,24,25-tetramethoxy-6,7,24,25-tetramethyl-14,17,32,35-tetra(propan-2-yloxy)-5,8,23,26-tetraoxa-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,9,11,13,15,17,19(39),20,22(27),28,30(37),31,33,35-pentadecaene
• CAS: 1215003-66-9
• 化学式: C₄₈H₅₈N₈O₁₂
• 分子量: 939.035
• InChiKey: OTIYWILGKHTJHU-MABAWHDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  68
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  220
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (6R,7R,24R,25R)-6,7,24,25-tetramethoxy-6,7,24,25-tetramethyl-14,17,32,35-tetra(propan-2-yloxy)-5,8,23,26-tetraoxa-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,9,11,13,15,17,19(39),20,22(27),28,30(37),31,33,35-pentadecaene 在 zinc diacetate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 以100%的产率得到
  参考文献：
  名称：

  Chiralbis-Acetal Porphyrazines as Near-infrared Optical Agents for Detection and Treatment of Cancer

  摘要：

  AbstractWe report the preparation of chiral oxygen atom‐appended porphyrazines (pzs) as biomedical optical agents that absorb and emit in the near‐IR wavelength range. These pzs take the form M[pz(A4‐nBn)], where “A” and “B” represent moieties appended to the pz’s pyrrole entities, A = (2R,3R) 2,3‐dimethyl‐2,3‐dimethoxy‐1,4‐diox‐2‐ene, B = β,β′‐di‐isopropoxybenzo, M is the incorporated metal ion (M = H2, Zn), and n = 0, 1, 2 (‐cis/‐trans) and 3 (Scheme 1). When dissolved in polar media, H2[pz(trans‐A2B2)] 5a does not fluoresce and has a negligible quantum yield for singlet oxygen generation (ФΔ = 0.074 ± 0.001, methanol), as measured by the photo‐oxidation of DMA. However, when sequestered in the nonpolar environment of a liposome, it displays strong NIR emission (λmax = 705 nm, Фf = 0.087) and an extremely high singlet oxygen quantum yield (ФΔ→1). Of this series, H2[pz(trans‐A2B2)] 5a is attractive as a potential optical probe, showing strongly fluorescent uptake by cells in culture, while 3‐[4,5‐dimethylthiazol‐2‐yl]‐2,5‐diphenyltetrazolium bromide measurements of cell viability show no evidence of dark toxicity. This agent does show significant photoinduced toxicity suggesting that pzs such as 5a have promise as “theranostic” optical agents that can be visualized with fluorescence imaging while acting as a sensitizer for photodynamic therapy. Synthesis of Porphyrazines 3a–7a, 3b–7b.image

  DOI：

  10.1111/j.1751-1097.2009.00681.x
• 作为产物：
  描述：

  1-imino-4,7-bis(1-methylethoxy)-1H-isoindolin-3-amine 、 (5R,6R)2,3-dicyano-5,6-dimethoxy-5,6-dimethyl-5,6-dihydro-1,4-dioxine 在 magnesium n-propoxide 、 溶剂黄146 、 sodium hydroxide 作用下， 以 丙醇 、 二氯甲烷 、 水 为溶剂， 反应 30.0h， 以3%的产率得到(6R,7R,15R,16R,24R,25R,33R,34R)-6,7,15,16,24,25,33,34-octamethoxy-6,7,15,16,24,25,33,34-octamethyl-5,8,14,17,23,26,32,35-octaoxa-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,9,11,13(18),19(39),20,22(27),28,30(37),31(36)-undecaene
  参考文献：
  名称：

  Chiralbis-Acetal Porphyrazines as Near-infrared Optical Agents for Detection and Treatment of Cancer

  摘要：

  AbstractWe report the preparation of chiral oxygen atom‐appended porphyrazines (pzs) as biomedical optical agents that absorb and emit in the near‐IR wavelength range. These pzs take the form M[pz(A4‐nBn)], where “A” and “B” represent moieties appended to the pz’s pyrrole entities, A = (2R,3R) 2,3‐dimethyl‐2,3‐dimethoxy‐1,4‐diox‐2‐ene, B = β,β′‐di‐isopropoxybenzo, M is the incorporated metal ion (M = H2, Zn), and n = 0, 1, 2 (‐cis/‐trans) and 3 (Scheme 1). When dissolved in polar media, H2[pz(trans‐A2B2)] 5a does not fluoresce and has a negligible quantum yield for singlet oxygen generation (ФΔ = 0.074 ± 0.001, methanol), as measured by the photo‐oxidation of DMA. However, when sequestered in the nonpolar environment of a liposome, it displays strong NIR emission (λmax = 705 nm, Фf = 0.087) and an extremely high singlet oxygen quantum yield (ФΔ→1). Of this series, H2[pz(trans‐A2B2)] 5a is attractive as a potential optical probe, showing strongly fluorescent uptake by cells in culture, while 3‐[4,5‐dimethylthiazol‐2‐yl]‐2,5‐diphenyltetrazolium bromide measurements of cell viability show no evidence of dark toxicity. This agent does show significant photoinduced toxicity suggesting that pzs such as 5a have promise as “theranostic” optical agents that can be visualized with fluorescence imaging while acting as a sensitizer for photodynamic therapy. Synthesis of Porphyrazines 3a–7a, 3b–7b.image

  DOI：

  10.1111/j.1751-1097.2009.00681.x

文献信息

• Porphyrazine Optical and Dual Optical/MR Contrast and Therapeutic Agents
  申请人：Barrett Anthony G.M.

  公开号：US20110293531A1

  公开（公告）日：2011-12-01

  Porphyrazines capable of localizing in a tumor of a mammal are disclosed. The porphyrazines are used in methods of imaging a tumor and in methods of treating tumors, either alone or in combination with a chemotherapeutic agent and/or radiation.