3-(2-nitro-1H-imidazol-1-yl)-N,N-bis((pyridin-2-yl)methyl)propan-1-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(2-nitro-1H-imidazol-1-yl)-N,N-bis((pyridin-2-yl)methyl)propan-1-amine
• 英文别名: 3-(2-nitroimidazol-1-yl)-N,N-bis(pyridin-2-ylmethyl)propan-1-amine
• 化学式: C₁₈H₂₀N₆O₂
• 分子量: 352.396
• InChiKey: ZQCRZTRAHBIJDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  92.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(99)technetium(I)(carbonyl)3(H2O)3] 、 3-(2-nitro-1H-imidazol-1-yl)-N,N-bis((pyridin-2-yl)methyl)propan-1-amine 以 aq. phosphate buffer 为溶剂， 反应 0.75h， 生成
  参考文献：
  名称：

  Modulation of in vivo distribution through chelator: Synthesis and evaluation of a 2-nitroimidazole–dipicolylamine–99mTc(CO)3 complex for detecting tumor hypoxia

  摘要：

  Previous studies have clearly demonstrated strong correlation between in vivo distribution and blood clearance of radiopharmaceuticals for the detection of hypoxia. Present study describes an attempt to improve the in vivo distribution of a previously reported 2-nitroimidazole-Tc-99m(CO)(3) complex by tuning its blood clearance pattern through structural modification of the ligand. Herein, a 2-nitroimidazole-dipicolylamine ligand (2-nitroimidazole-DPA) was synthesized in a two-step procedure and radiolabeled with Tc-99m(CO)(3) core. Subsequently, the complex was evaluated in Swiss mice bearing fibrosarcoma tumor. As intended by its design, 2-nitroimidazole-DPA-Tc-99m(CO)(3) complex was more lipophilic than previously reported 2-nitroimidazole-DETA-Tc-99m(CO)(3) complex (DETA-diethylenetriamine) and showed slower blood clearance. Consequently it showed higher tumor uptake than 2-nitroimidazole-DETA-Tc-99m(CO)(3) complex. Significantly, despite structural modifications, other parameters such as the tumor to blood ratio and tumor to muscle ratio of the 2-nitroimidazole-DPA-Tc-99m(CO)(3) complex remained comparable to that of 2-nitroimidazole-DETA-Tc-99m(CO)(3) complex. Present study demonstrates the feasibility of structural modifications for improving in vivo tumor uptake of hypoxia detecting radiopharmaceuticals. This might encourage researchers to improve suboptimal properties of a potential radiopharmaceuticals rather than ignoring it altogether. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.034
• 作为产物：
  描述：

  二甲基吡啶胺 、 1-(3-bromopropyl)-2-nitro-1H-imidazole 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以55%的产率得到3-(2-nitro-1H-imidazol-1-yl)-N,N-bis((pyridin-2-yl)methyl)propan-1-amine
  参考文献：
  名称：

  走向低氧选择性R和Tri三羰基配合物

  摘要：

  为了制备缺氧选择性成像和治疗剂，已经制备了carbonyl（I）和rh（I）与吡啶hydr，二吡啶胺和含有硝基苄基或硝基咪唑官能团的吡啶基氨基羧酸酯配体的三羰基配合物。使用微波辐射以短的反应时间合成了三羰基rh络合物。具有去质子化的对硝基苯基吡啶基ligand配体的三羰基hen配合物发光，并且已使用共聚焦荧光显微镜技术将其用于HeLa细胞中的摄取。与低氧细胞相比，所选的三羰基rh络合物在低氧细胞中显示出更高的摄取。A 99m具有携带硝基咪唑官能团的二吡啶基胺配体的Tc三羰基配合物在人血清中稳定，并显示其位于小鼠的人肾细胞癌（RCC; SK-RC-52）肿瘤中。

  DOI：

  10.1021/acs.inorgchem.5b01691

文献信息

• Toward Hypoxia-Selective Rhenium and Technetium Tricarbonyl Complexes
  作者：Andrea J. North、David J. Hayne、Christine Schieber、Katherine Price、Anthony R. White、Peter J. Crouch、Angela Rigopoulos、Graeme J. O’Keefe、Henri Tochon-Danguy、Andrew M. Scott、Jonathan M. White、Uwe Ackermann、Paul S. Donnelly

  DOI：10.1021/acs.inorgchem.5b01691

  日期：2015.10.5

  hypoxia-selective imaging and therapeutic agents, technetium(I) and rhenium(I) tricarbonyl complexes with pyridylhydrazone, dipyridylamine, and pyridylaminocarboxylate ligands containing nitrobenzyl or nitroimidazole functional groups have been prepared. The rhenium tricarbonyl complexes were synthesized with short reaction times using microwave irradiation. Rhenium tricarbonyl complexes with deprotonated

  为了制备缺氧选择性成像和治疗剂，已经制备了carbonyl（I）和rh（I）与吡啶hydr，二吡啶胺和含有硝基苄基或硝基咪唑官能团的吡啶基氨基羧酸酯配体的三羰基配合物。使用微波辐射以短的反应时间合成了三羰基rh络合物。具有去质子化的对硝基苯基吡啶基ligand配体的三羰基hen配合物发光，并且已使用共聚焦荧光显微镜技术将其用于HeLa细胞中的摄取。与低氧细胞相比，所选的三羰基rh络合物在低氧细胞中显示出更高的摄取。A 99m具有携带硝基咪唑官能团的二吡啶基胺配体的Tc三羰基配合物在人血清中稳定，并显示其位于小鼠的人肾细胞癌（RCC; SK-RC-52）肿瘤中。
• Modulation of in vivo distribution through chelator: Synthesis and evaluation of a 2-nitroimidazole–dipicolylamine–99mTc(CO)3 complex for detecting tumor hypoxia
  作者：Madhava B. Mallia、Sweety Mittal、Haladhar D. Sarma、Sharmila Banerjee

  DOI：10.1016/j.bmcl.2015.11.034

  日期：2016.1

  Previous studies have clearly demonstrated strong correlation between in vivo distribution and blood clearance of radiopharmaceuticals for the detection of hypoxia. Present study describes an attempt to improve the in vivo distribution of a previously reported 2-nitroimidazole-Tc-99m(CO)(3) complex by tuning its blood clearance pattern through structural modification of the ligand. Herein, a 2-nitroimidazole-dipicolylamine ligand (2-nitroimidazole-DPA) was synthesized in a two-step procedure and radiolabeled with Tc-99m(CO)(3) core. Subsequently, the complex was evaluated in Swiss mice bearing fibrosarcoma tumor. As intended by its design, 2-nitroimidazole-DPA-Tc-99m(CO)(3) complex was more lipophilic than previously reported 2-nitroimidazole-DETA-Tc-99m(CO)(3) complex (DETA-diethylenetriamine) and showed slower blood clearance. Consequently it showed higher tumor uptake than 2-nitroimidazole-DETA-Tc-99m(CO)(3) complex. Significantly, despite structural modifications, other parameters such as the tumor to blood ratio and tumor to muscle ratio of the 2-nitroimidazole-DPA-Tc-99m(CO)(3) complex remained comparable to that of 2-nitroimidazole-DETA-Tc-99m(CO)(3) complex. Present study demonstrates the feasibility of structural modifications for improving in vivo tumor uptake of hypoxia detecting radiopharmaceuticals. This might encourage researchers to improve suboptimal properties of a potential radiopharmaceuticals rather than ignoring it altogether. (C) 2015 Elsevier Ltd. All rights reserved.