5-iodo-6-nitro-2-(N-tert-butyloxycarbonylpiperazin-1-yl)quinoline | 159532-00-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-iodo-6-nitro-2-(N-tert-butyloxycarbonylpiperazin-1-yl)quinoline
• 英文别名: Tert-butyl 4-(5-iodo-6-nitroquinolin-2-yl)piperazine-1-carboxylate
• CAS: 159532-00-0
• 化学式: C₁₈H₂₁IN₄O₄
• 分子量: 484.294
• InChiKey: HGGOIVJEBRXPOK-UHFFFAOYSA-N

物化性质

• 沸点：
  580.9±50.0 °C(predicted)
• 密度：
  1.607±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  91.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-iodo-6-nitro-2-(N-tert-butyloxycarbonylpiperazin-1-yl)quinoline 在 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 5-iodo-6-nitro-2-(piperazin-1-yl)quinoline
  参考文献：
  名称：

  Synthesis of 123I-and labelled 5-iodo-6-nitroquipazine

  摘要：

  报告了强效和选择性 5-羟色胺再摄取复合放射性配体 [123I]- 和 [125I]5-iodo-6- 硝基喹嗪（5-iodo-6-nitro-2-piperazinylquinoline）的合成。通过七步合成顺序，提供了 BOC 保护的 5-三丁基锡-6-硝基喹嗪前体，用于放射性碘化。合成结束时，123I 和 125I 的放射性碘化率分别为 40% 和 60%，得到的标记产物具有很高的比活度（分别大于 4000 和大于 2000 Ci/mmol）和放射化学纯度（大于 98%）。

  DOI：

  10.1002/jlcr.2580341003
• 作为产物：
  描述：

  2-chloro-5-iodoquinoline 在 硫酸 、 硝酸 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 5-iodo-6-nitro-2-(N-tert-butyloxycarbonylpiperazin-1-yl)quinoline
  参考文献：
  名称：

  Synthesis of a fluorine-18-labelled derivative of 6-nitroquipazine, as a radioligand for the In vivo serotonin transporter imaging with PET

  摘要：

  Considerable efforts have been engaged in the design, synthesis and pharmacological characterization of radioligands for imaging the serotonin transporter, based on its implication in several neuropsychiatric diseases, Such as depression, anxiety and schizophrenia. In the 5-halo-6-nitroquipazine series, the fluoro derivative has been designed for positron emission tomography (PET). The corresponding 5-iodo-, 5-bromo- and 5-chloro N-Boc-protected quipazines as labelling precursors, as well as 5-fluoro-6-nitroquipazine as a reference compound have been synthesized. 5-[F-18]Fluoro-6-nitroquipazine has been radiolabelled with fluorine-18 (positron-emitting isotope, 109.8 min half-life) by nucleophilic aromatic substitution from the corresponding N-Boc protected 5-bromo- and 5-chloro-precursors using K[F-18]F-K-222 complex in DMSO by conventional heating (145degreesC, 2 min) or microwave activation (50 W, 30-45 s), followed by removal of the protective group with TFA. Typically, 15-25 mCi (5.5-9.2 GBq) of 5-[F-18]fluoro-6-nitroquipazine (1-2 Ci/mumol or 37-72 GBq/mumol) could be obtained in 70-80 min starting from a 550-650 mCi (20.3-24.0 GBq) aliquot of a cyclotron [F-18]F- production batch (2.7-3.8% non decay-corrected yield based on the starting [F-18]fluoride). Ex vivo studies (biodistribution in rat), as well as PET imaging (in monkey) demonstrated that 5-[(18)]fluoro-6-nitroquipazine ([F-18]-1d) readily crossed the blood brain barrier and accumulated in the regions rich in 5-HT transporter (frontal-and posterial cortex, striata). However, the low accumulation of the tracer in the thalamus (rat and monkey) as well as the comparable displacement of the tracer observed with both citalopram, a reference 5-HT re-uptake inhibitor and maprotiline, a norepinephrine re-uptake inhibitor (rat), indicate that 5-[F-18]fluoro-6-nitroquipazine ([F-18]-1d) does not have the suggested potential for PFT imaging of the serotin transporter (SERT). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00098-6