N-(5-氨基戊基)-邻苯二甲酰亚胺盐酸盐 | 7292-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 中文名称: N-(5-氨基戊基)-邻苯二甲酰亚胺盐酸盐
• 英文名称: N-(5-aminopentyl)phthalimide hydrochloride
• 英文别名: 5-phthalimidopentylamine hydrochloride；2-(5-aminopentyl)isoindole-1,3-dione;hydron;chloride
• CAS: 7292-63-9
• 化学式: C₁₃H₁₆N₂O₂*ClH
• mdl: MFCD08448237
• 分子量: 268.743
• InChiKey: FGJDPHUEWISYHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  63.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2925190090

反应信息

• 作为反应物：
  描述：

  N-(5-氨基戊基)-邻苯二甲酰亚胺盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis and Bioevaluation of Novel [¹⁸F]FDG-Conjugated 2-Nitroimidazole Derivatives for Tumor Hypoxia Imaging

  摘要：

  Hypoxia imaging can guide tumor treatment and monitor changes in hypoxia during treatment. However, there is still no ideal hypoxia imaging agent for clinical applications. In this study, two novel 2-nitromidazole derivatives were synthesized and directly radiolabeled by [F-18]FDG in high radiochemical yield and excellent radiochemical purity. Cell experiments, biodistribution, and positron emission tomography (PET) imaging studies were also conducted in mice-bearing S180 or OS732 tumors. [F-18]FDG-2NNC2ON [(2R,3S,4R,E)-2-F-18-fluoro-3,4,5,6-tetrahydroxyhexanal O-3-(2-(2-nitro-1H-imidazole-1-yl)ethylamino)-2-oxopropyl oxime] and [F-18]FDG-2NNCSON [(2R,3S,4R,E)-2-F-18-fluoro-3,4,5,6-tetrahydroxyhexanal-O-3-(5-(2-nitro-1H-imidazole-1-yl)entylamino)-2-oxopropyl oxime] can be cleared from the blood quickly and specifically target hypoxic tumor cells. The uptake of the probes by hypoxic cells gradually increases with time. After 4 h, the uptake value of [F-18]FDG-2NNC2ON in hypoxic cells is 3.2 times higher than that in normoxia cells. In contrast, there is no difference in the uptake of [F-18]FDG between hypoxic cells and normoxia cells. Biodistribution resulting from two tumor models indicate that the uptake values of the two radiotracers in the tumor are higher at 1 h than those at 2 and 4 h. At 1 and 2 h, the tumors are clearly observed on the PET images and the imaging features of [F-18]FDG-2NNC5ON and [F-18]FDG-2NNC2ON are distinct from those of [F-18]FDG. Compared with [F-18]FDG-2NNC5ON, [F-18]FDG-2NNC2ON has a higher proportion of renal excretion, lower digestive tract uptake, and better imaging contrast because of its higher hydrophilicity. At 2 h, [F-18]FDG-2NNC2ON shows a good tumor-to-blood (T/B) ratio, tumor-to-muscle ratio based on biodistribution (Bio-T/M ratio), and tumor-to-muscle ratio based on regions of interest on the PET images [region of interest (ROI)-T/M ratio] in the two tumor models (T/B, Bio-T/M, and ROI-T/M ratios are 3.2, 2.6, and 3.9 in the S180 tumor model and are 3.4, 4.2, and 4.6 in the OS732 tumor model, respectively). The imaging features visualized with autoradiography mostly coincided with the positive areas of HIF1 alpha staining by immunofluorescence. Meanwhile, the biodistribution study and PET imaging revealed that the uptake of the radiotracers in the tumor cannot be competed by 5% glucose, confirming that [F-18]FDG-2NNC2ON targets the hypoxic regions of the tumors instead of targeting tumors through the glucose metabolism pathway. These results suggest that the new 2-nitroimidazole derivative conjugated with [F-18]FDG, [F-18]FDG-2NNC2ON, has potential as an imaging agent for hypoxia.

  DOI：

  10.1021/acs.molpharmaceut.9b00075
• 作为产物：
  描述：

  N-(5-溴戊基)邻苯二甲酰亚胺 在 hydrochloric acid diethyl ether 、 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 N-(5-氨基戊基)-邻苯二甲酰亚胺盐酸盐
  参考文献：
  名称：

  Synthesis and Bioevaluation of Novel [¹⁸F]FDG-Conjugated 2-Nitroimidazole Derivatives for Tumor Hypoxia Imaging

  摘要：

  Hypoxia imaging can guide tumor treatment and monitor changes in hypoxia during treatment. However, there is still no ideal hypoxia imaging agent for clinical applications. In this study, two novel 2-nitromidazole derivatives were synthesized and directly radiolabeled by [F-18]FDG in high radiochemical yield and excellent radiochemical purity. Cell experiments, biodistribution, and positron emission tomography (PET) imaging studies were also conducted in mice-bearing S180 or OS732 tumors. [F-18]FDG-2NNC2ON [(2R,3S,4R,E)-2-F-18-fluoro-3,4,5,6-tetrahydroxyhexanal O-3-(2-(2-nitro-1H-imidazole-1-yl)ethylamino)-2-oxopropyl oxime] and [F-18]FDG-2NNCSON [(2R,3S,4R,E)-2-F-18-fluoro-3,4,5,6-tetrahydroxyhexanal-O-3-(5-(2-nitro-1H-imidazole-1-yl)entylamino)-2-oxopropyl oxime] can be cleared from the blood quickly and specifically target hypoxic tumor cells. The uptake of the probes by hypoxic cells gradually increases with time. After 4 h, the uptake value of [F-18]FDG-2NNC2ON in hypoxic cells is 3.2 times higher than that in normoxia cells. In contrast, there is no difference in the uptake of [F-18]FDG between hypoxic cells and normoxia cells. Biodistribution resulting from two tumor models indicate that the uptake values of the two radiotracers in the tumor are higher at 1 h than those at 2 and 4 h. At 1 and 2 h, the tumors are clearly observed on the PET images and the imaging features of [F-18]FDG-2NNC5ON and [F-18]FDG-2NNC2ON are distinct from those of [F-18]FDG. Compared with [F-18]FDG-2NNC5ON, [F-18]FDG-2NNC2ON has a higher proportion of renal excretion, lower digestive tract uptake, and better imaging contrast because of its higher hydrophilicity. At 2 h, [F-18]FDG-2NNC2ON shows a good tumor-to-blood (T/B) ratio, tumor-to-muscle ratio based on biodistribution (Bio-T/M ratio), and tumor-to-muscle ratio based on regions of interest on the PET images [region of interest (ROI)-T/M ratio] in the two tumor models (T/B, Bio-T/M, and ROI-T/M ratios are 3.2, 2.6, and 3.9 in the S180 tumor model and are 3.4, 4.2, and 4.6 in the OS732 tumor model, respectively). The imaging features visualized with autoradiography mostly coincided with the positive areas of HIF1 alpha staining by immunofluorescence. Meanwhile, the biodistribution study and PET imaging revealed that the uptake of the radiotracers in the tumor cannot be competed by 5% glucose, confirming that [F-18]FDG-2NNC2ON targets the hypoxic regions of the tumors instead of targeting tumors through the glucose metabolism pathway. These results suggest that the new 2-nitroimidazole derivative conjugated with [F-18]FDG, [F-18]FDG-2NNC2ON, has potential as an imaging agent for hypoxia.

  DOI：

  10.1021/acs.molpharmaceut.9b00075

文献信息

• [EN] FUNCTIONALIZED LINEAR LIGANDS AND COMPLEXES THEREOF<br/>[FR] LIGANDS LINÉAIRES FONCTIONNALISÉS ET COMPLEXES DE CEUX-CI
  申请人：LUMIPHORE INC

  公开号：WO2016106241A1

  公开（公告）日：2016-06-30

  The invention relates to chemical compounds and complexes that can be used in therapeutic and diagnostic applications.

  这项发明涉及可用于治疗和诊断应用的化合物和配合物。
• .omega.-(Arylsulfonamido)-alkylamine
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US04069254A1

  公开（公告）日：1978-01-17

  .omega.-(Arylsulfonamido)-alkylamines having the formula R'-SO.sub.2 NH(CH.sub.2).sub.n R I wherein R represents an amino group which can be acylated; R' represents phenyl or naphthyl which can be substituted by halogen or lower alkyl; and n represents an integer from 5 - 8 are effective in inhibiting blood platelet aggregation.

  具有以下公式的.omega.-(芳基磺酰胺基)-烷基胺类化合物 R'-SO.sub.2 NH(CH.sub.2).sub.n R I，其中 R 代表可酰化的氨基团；R' 代表苯基或萘基，可被卤素或较低烷基取代；n 代表5-8之间的整数，对抑制血小板聚集有效。
• Functionalized linear ligands and complexes thereof
  申请人：LUMIPHORE, INC.

  公开号：US10434186B2

  公开（公告）日：2019-10-08

  The invention relates to chemical compounds and complexes that can be used in therapeutic and diagnostic applications.

  本发明涉及可用于治疗和诊断的化合物和复合物。
• FUNCTIONALIZED LINEAR LIGANDS AND COMPLEXES THEREOF
  申请人：Lumiphore, Inc.

  公开号：EP3237429A1

  公开（公告）日：2017-11-01
• US4069254A
  申请人：——

  公开号：US4069254A

  公开（公告）日：1978-01-17