3-(3-aminopropyl)thymidine | 439600-38-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 3-(3-aminopropyl)thymidine
• 英文别名: 3-(3-aminopropyl)-1-((2R,4S,5R)-4-hydroxy)-5-((hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS: 439600-38-1
• 化学式: C₁₃H₂₁N₃O₅
• 分子量: 299.327
• InChiKey: HBUAAPFABIFRMX-HBNTYKKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.69
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  119.71
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-(3-aminopropyl)thymidine 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Kinase-mediated trapping of bi-functional conjugates of paclitaxel or vinblastine with thymidine in cancer cells

  摘要：

  In the present work, we explore the possibility of introducing selectivity to existing chernotherapeutics via the design of non-pro-drug, bi-functional molecules comprising a microtubule-binding agent and a substrate for a disease-associated kinase. The design, synthesis, and in vitro biological evaluation of paclitaxel thymidine and vinblastine-thymidine bi-functional conjugates are reported here. This work provides the first account of 'kinase-mediated trapping' of cancer therapeutics. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.07.003
• 作为产物：
  描述：

  beta-胸苷 在 钾硼氢 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 2.0h， 生成 3-(3-aminopropyl)thymidine
  参考文献：
  名称：

  胸腺嘧啶激酶1-靶向的硼烷嘧啶核苷核苷类似物的合成及评估，用于硼中子俘获疗法的癌症

  摘要：

  合成了十六个第二代氨基和酰胺基取代的碳硼烷基嘧啶核苷类似物的文库，并设计为可用于癌症的硼中子捕获疗法（BNCT）的胸苷激酶1（TK1）的底物和抑制剂，并通过酶动力学进行了评估-，酶抑制-，代谢组学和生物分布研究。这些第二代碳硼烷基嘧啶核苷类似物（YB18A [ 3 ]）中的一个，氨基直接与通过乙烯间隔基束缚在胸腺嘧啶3位上的间甲碳氢化合物笼相连，具有约3-4倍的底物hTK1和抑制剂比N5 - 2OH（2-），是第一代碳硼烷基嘧啶核苷类似物。既2和3似乎是5'-单磷酸化在TK1（+）细胞RG2，无论在体外和体内。对携带脑内RG2神经胶质瘤的大鼠进行生物分布研究后，选择性摄取了3种肿瘤，瘤内浓度大约是2种的4倍。获得的结果大大提高了对TK1和碳硼烷基嘧啶核苷类似物之间结合相互作用的理解，并将深刻影响这些试剂的未来设计策略。

  DOI：

  10.1016/j.ejmech.2015.05.042

文献信息

• Novel ^99mTc-labelled complexes with thymidine isocyanide: radiosynthesis and evaluation as potential tumor imaging tracers
  作者：Xiaojiang Duan、Xuran Zhang、Qianqian Gan、Si'an Fang、Qing Ruan、Xiaoqing Song、Junbo Zhang

  DOI：10.1039/c7md00635g

  日期：——

  A novel thymidine isocyanide (CN-TdR) functionalized at the N3 position of thymidine was synthesized and then radiolabelled with 99mTc(I) and [99mTc(I)(CO)3]+ cores to produce [99mTc(CN-TdR)6]+ and [99mTc(CO)3(CN-TdR)3]+, respectively. Both of them were prepared with high radiochemical purity and were stable over 6 h in saline at ambient temperature and in serum at 37 °C. The partition coefficient

  合成了一种在胸苷N3位功能化的新型胸苷异氰化物（CN-TdR），然后用99m Tc( I ) 和 [ 99m Tc ( I )(CO) 3 ] +核心进行放射性标记，产生[ 99m Tc(CN-TdR) ) 6 ] +和[ 99m Tc(CO) 3 (CN-TdR) 3 ] +，分别。两者均具有高放射化学纯度，并且在环境温度的盐水和 37°C 的血清中稳定超过 6 小时。分配系数结果表明它们是亲水性的。细胞内化研究表明，它们的摄取可能是由核苷转运蛋白介导的。这些复合物在携带 S180 肿瘤的小鼠中的生物分布表明，它们在肿瘤中以高摄取量积累，并从血液和肌肉中迅速清除，产生高肿瘤/血液和肿瘤/肌肉比率。其中，[ 99m Tc(CN-TdR) 6 ] +在注射后 60 分钟时表现出较高的肿瘤摄取、肿瘤/血液比率和肿瘤/肌肉比率的优势。单光子发射计算机断层扫描成像研究表明，肿瘤部位有明显的积累，表明[
• Radiosynthesis and evaluation of novel 99mTc(CO)3-labelled thymidine dithiocarbamate derivatives for tumor imaging with SPECT
  作者：Xiaojiang Duan、Qing Ruan、Qianqian Gan、Xiaoqing Song、Si'an Fang、Xuran Zhang、Junbo Zhang

  DOI：10.1016/j.jorganchem.2018.05.009

  日期：2018.8

  A series of novel thymidine dithiocarbamate derivatives (DTC-TdR) were successfully synthesized and then radiolabelled using [Tc-99m(CO)(3)](+) core with high yields. The chemical characterizations of Tc-99m(CO)(3)-labelled dithiocarbamate derivatives have been carried out by preparing their corresponding rhenium complexes. The radiotracers were stable in vitro, and the partition co efficient results indicated that they were lipophilic. The cell uptake studies showed the uptakes of these(99m)Tc(CO)(3)-labelled thymidine derivatives were mediated by nucleoside transporters. Biodistribution of the complexes in mice bearing tumor showed that they had high tumor uptake and good tumor/muscle ratio. A clear SPECT imaging of the tumor location was obtained in mice bearing S180 tumor with one of radiotracers, suggesting they would be potential tumor imaging agents. (C) 2018 Elsevier B.V. All rights reserved.