3-(4-aminobutyl)thymidine | 912757-89-2

• 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-(4-aminobutyl)thymidine
• CAS: 912757-89-2
• 化学式: C₁₄H₂₃N₃O₅
• 分子量: 313.354
• InChiKey: CYONJIMQFFTJAQ-QJPTWQEYSA-N

物化性质

• 沸点：
  532.1±60.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 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-(4-aminobutyl)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 palladium on activated charcoal 氢气 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 3-(4-aminobutyl)thymidine
  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

文献信息

• Synthesis and evaluation of thymidine kinase 1-targeting carboranyl pyrimidine nucleoside analogs for boron neutron capture therapy of cancer
  作者：Hitesh K. Agarwal、Ahmed Khalil、Keisuke Ishita、Weilian Yang、Robin J. Nakkula、Lai-Chu Wu、Tehane Ali、Rohit Tiwari、Youngjoo Byun、Rolf F. Barth、Werner Tjarks

  DOI：10.1016/j.ejmech.2015.05.042

  日期：2015.7

  amido-substituted carboranyl pyrimidine nucleoside analogs, designed as substrates and inhibitors of thymidine kinase 1 (TK1) for potential use in boron neutron capture therapy (BNCT) of cancer, was synthesized and evaluated in enzyme kinetic-, enzyme inhibition-, metabolomic-, and biodistribution studies. One of these 2nd generation carboranyl pyrimidine nucleoside analogs (YB18A [3]), having an amino group directly

  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。
• 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.