[¹⁸F]-3-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-6-fluorodibenzo[b,d]thiophene 5,5-dioxide | 1456878-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: [¹⁸F]-3-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-6-fluorodibenzo[b,d]thiophene 5,5-dioxide
• 英文别名: 3-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-6-[¹⁸F]fluorodibenzo[b,d]thiophene-5,5-dioxide；Asem F-18；3-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-6-(18F)fluoranyldibenzothiophene 5,5-dioxide
• CAS: 1456878-52-6
• 化学式: C₁₉H₁₉FN₂O₂S
• 分子量: 357.438
• InChiKey: JIGWWGDIEUWCOR-LRFGSCOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  49
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-6-nitrodibenzo[b,d]thiophene 5,5-dioxide 在 fluorine-18 、 potassium hydrogencarbonate 、 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 二甲基亚砜 为溶剂， 反应 0.04h， 生成 [¹⁸F]-3-(1,4-diazabicyclo[3.2.2]nonan-4-yl)-6-fluorodibenzo[b,d]thiophene 5,5-dioxide
  参考文献：
  名称：

  [18F]ASEM 的微波辅助放射合成，一种放射性标记的α7-烟碱乙酰胆碱受体拮抗剂

  摘要：

  报道了 [(18) F]ASEM（一种 α7-烟碱型乙酰胆碱能受体放射性配体）的原始放射化学合成的改进。新程序利用微波辅助放射性氟化。此外，还开发了一种新的制备型 HPLC 方法来消除最终产品中的化学杂质。质量控制程序也得到了加强，以提高对潜在杂质的分辨率的产品检测。[(18) F]ASEM 的非衰变校正 (NDC) 产率为 20.1 ± 8.9%，平均合成时间为 57 分钟，平均比放射性为 856 ± 332 GBq/µmol (23 ± 9 Ci/µmol) .

  DOI：

  10.1002/jlcr.3275

文献信息

• DERIVATIVES OF DIBENZOTHIOPHENE IMAGING OF alpha-7 NICOTINIC ACETYLCHOLINE RECEPTORS
  申请人：THE JOHNS HOPKINS UNIVERSITY

  公开号：US20160235869A1

  公开（公告）日：2016-08-18

  The presently disclosed subject matter provides non-invasive methods for imaging, quantifying α7 nicotinic cholinergic receptors, and diagnosing a disease or condition associated with α7-nAChRs. Methods for preparing radiolabeled derivatives of dibenzothiophene and compounds provided thereof also are provided.

  目前披露的主题提供了非侵入性的成像方法，量化α7烟碱性胆碱受体，并诊断与α7-nAChRs相关的疾病或病况。还提供了制备二苯并噻吩的放射性标记衍生物和所提供化合物的方法。
• Derivatives of Dibenzothiophene for Positron Emission Tomography Imaging of α7-Nicotinic Acetylcholine Receptors
  作者：Yongjun Gao、Kenneth J. Kellar、Robert P. Yasuda、Thao Tran、Yingxian Xiao、Robert F. Dannals、Andrew G. Horti

  DOI：10.1021/jm401184f

  日期：2013.10.10

  A new series of derivatives of 3-(1,4-diazabicyclo[3.2.2]nonan-4-yl)dibenzo[b,d]thiophene 5,5-dioxide with high binding affinities and selectivity for alpha 7-nicotinic acetylcholine receptors (alpha 7-nAChRs) (K-i = 0.4-20 nM) has been synthesized for positron emission tomography (PET) imaging of alpha 7-nAChRs. Two radiolabeled members of the series [F-18]7a (K-i = 0.4 nM) and [F-18]7c (K-i = 1.3 nM) were synthesized. [F-18]7a and [F-18]7c readily entered the mouse brain and specifically labeled alpha 7-nAChRs. The alpha 7-nAChR selective ligand 1 (SSR180711) blocked the binding of [F-18]7a in the mouse brain in a dose-dependent manner. The mouse blocking studies with non-alpha 7-nAChR central nervous system drugs demonstrated that [F-18]7a is highly alpha 7-nAChR selective. In agreement with its binding affinity the binding potential of [F-18]7a (BPND = 5.3-8.0) in control mice is superior to previous alpha 7-nAChR PET radioligands. Thus, [F-18]7a displays excellent imaging properties in mice and has been chosen for further evaluation as a potential PET radioligand for imaging of alpha 7-nAChR in non-human primates.