5-bromo-6-nitro-2-(piperazin-1-yl)quinoline | 159531-98-3

• 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-bromo-6-nitro-2-(piperazin-1-yl)quinoline
• 英文别名: 5-bromo-6-nitro-2-piperazinylquinoline；5-bromo-6-nitroquipazine；5-bromo-6-nitro-2-piperazin-1-ylquinoline
• CAS: 159531-98-3
• 化学式: C₁₃H₁₃BrN₄O₂
• 分子量: 337.176
• InChiKey: ZVGUGUOQECOEHR-UHFFFAOYSA-N

物化性质

• 沸点：
  496.3±40.0 °C(Predicted)
• 密度：
  1.582±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  74
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-bromo-6-nitro-2-(piperazin-1-yl)quinoline 生成 8-bromo-6-nitroquipazine
  参考文献：
  名称：

  Substituted 6-nitroquipazines, methods of preparation, and methods of use

  摘要：

  本发明公开了一种式为##STR1## 的取代6-硝基喹嗪，其中R.sub.1、R.sub.2、R.sub.3和R.sub.4分别选自H、Fl、Cl、Br、I、CF.sub.3、CH.sub.2 CH.sub.2 F、CH.sub.3、CH.sub.2 CH.sub.3和--CH(CH.sub.3).sub.2的群组，其中R.sub.1、R.sub.2、R.sub.3和R.sub.4中的一个不是H。本发明还公开了一种测量样品中5-羟色胺摄取位点的方法，其中将放射性配体与样品孵育，然后测定配体与样品结合的放射性，并利用放射性标记的取代6-硝基喹嗪作为放射性配体。本发明还公开了一种制造方法和使用方法。

  公开号：

  US05372813A1
• 作为产物：
  描述：

  5-溴喹啉 在 过氧乙酸 、 硫酸 、 硝酸 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 5.75h， 生成 5-bromo-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

文献信息

• Synthesis of 123I-and labelled 5-iodo-6-nitroquipazine
  作者：Chester A. Mathis、Joel D. Enas、Stephen M. Hanrahan、Eyup Akgün

  DOI：10.1002/jlcr.2580341003

  日期：1994.10

  The syntheses of the potent and selective serotonin reuptake complex radioligands [123I]- and [125I]5-iodo-6-nitroquipazine (5-iodo-6-nitro-2-piperazinylquinoline) are reported. A seven step synthetic sequence provided the BOC-protected 5-tributyltin-6-nitroquipazine precursor for radioiodination. End of synthesis radioiodination yields of ∼40% for 123I and ∼60% for 125I were achieved resulting in labelled products with high specific activities (>4000 and >2000 Ci/mmol, respectively) and radiochemical purities (>98%).

  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%）。
• US5372813A
  申请人：——

  公开号：US5372813A

  公开（公告）日：1994-12-13
• Synthesis of a fluorine-18-labelled derivative of 6-nitroquipazine, as a radioligand for the In vivo serotonin transporter imaging with PET
  作者：Mylène Karramkam、Frédéric Dollé、Héric Valette、Laurent Besret、Yann Bramoullé、Françoise Hinnen、Françoise Vaufrey、Carine Franklin、Sébastien Bourg、Christine Coulon、Michèle Ottaviani、Marcel Delaforge、Christian Loc'h、Michel Bottlaender、Christian Crouzel

  DOI：10.1016/s0968-0896(02)00098-6

  日期：2002.8

  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.
• Substituted 6-nitroquipazines, methods of preparation, and methods of use
  申请人：The Regents, University of California

  公开号：US05372813A1

  公开（公告）日：1994-12-13

  Disclosed is a substituted 6-nitroquipazine of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are each selected from the group consisting of H, Fl, CL, Br, I, CF.sub.3, CH.sub.2 CH.sub.2 F, CH.sub.3, CH.sub.2 CH.sub.3, and --CH(CH.sub.3).sub.2, and wherein one of R.sub.1, R.sub.2, R.sub.3, and R.sub.4 is other than H. Also disclosed is a method for measurement of serotonin uptake sites in a sample, in which a radioligand is incubated with a sample and then the radioactivity of the radioligand bound to the sample is determined, utilizing a radio labeled substituted 6-nitroquipazine as the radioligand. Also disclosed is a method of manufacture and method of use.

  本发明公开了一种式为##STR1## 的取代6-硝基喹嗪，其中R.sub.1、R.sub.2、R.sub.3和R.sub.4分别选自H、Fl、Cl、Br、I、CF.sub.3、CH.sub.2 CH.sub.2 F、CH.sub.3、CH.sub.2 CH.sub.3和--CH(CH.sub.3).sub.2的群组，其中R.sub.1、R.sub.2、R.sub.3和R.sub.4中的一个不是H。本发明还公开了一种测量样品中5-羟色胺摄取位点的方法，其中将放射性配体与样品孵育，然后测定配体与样品结合的放射性，并利用放射性标记的取代6-硝基喹嗪作为放射性配体。本发明还公开了一种制造方法和使用方法。