ST-928 | 1158961-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ST-928
• 英文别名: 1-(4-(3-(Piperidin-1-yl)propoxy)benzyl)piperidin-4-yl methanesulfonate；[1-[[4-(3-piperidin-1-ylpropoxy)phenyl]methyl]piperidin-4-yl] methanesulfonate
• CAS: 1158961-47-7
• 化学式: C₂₁H₃₄N₂O₄S
• 分子量: 410.578
• InChiKey: AWJRAHLZDXQGMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  67.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ST-928 在 potassium [¹⁸F]fluoride 、 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 水 、 乙腈 为溶剂， 反应 0.5h， 以20%的产率得到(18)F-ST-889
  参考文献：
  名称：

  Radiofluorinated histamine H3 receptor antagonist as a potential probe for in vivo PET imaging: Radiosynthesis and pharmacological evaluation

  摘要：

  The histamine H-3 receptor (H3R) plays a role in cognition and memory processes and is implicated in different neurological disorders, including Alzheimer's disease, schizophrenia, and narcolepsy. In vivo studies of the H3R occupancy using a radiolabeled PET tracer would be very useful for CNS drug discovery and development. We report here the radiosynthesis, in vitro and in vivo evaluation of a novel F-18-labeled high-affinity H3R antagonist F-18-ST889. The radiosynthesis was accomplished via nucleophilic substitution of the mesylate leaving group with a radiochemical yield of 8-20%, radiochemical purity >99%, and specific radioactivity >65 GBq/mu mol. F-18-ST889 exhibited high in vivo stability and rather low lipophilicity (logD(7.4) = 0.35 +/- 0.09). In vitro autoradiography showed specific binding in H3R-rich brain regions such as striatum and cortex. However, in vivo PET imaging of the rat brain with F-18-ST889 was not successful. Possible reasons are discussed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.024
• 作为产物：
  描述：

  甲基磺酰氯 、 1-(4-(3-piperidin-1-yl-propoxy)benzyl)piperidin-4-ol 以 二氯甲烷 为溶剂， 生成 ST-928
  参考文献：
  名称：

  Fluorinated non-imidazole histamine H3 receptor antagonists

  摘要：

  Fluorine substituents have become a widespread and important component in drug design and development. Here, the synthesis of fluorine containing compounds and some corresponding precursor molecules are presented for potential isotope labelling as well as their data obtained with in vitro and in vivo screenings. The compounds vary in the basic centres (piperidine or pyrrolidine) and are fluoro substituted in different positions of the basic alicyclic moiety. Pharmacological evaluation resulted in ligands with high affinities at hH(3) receptor in the nanomolar and subnanomolar concentration range and some with high antagonist in vivo potencies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.110