2-chloro-5-iodoquinoline | 455955-26-7

• 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: 2-chloro-5-iodoquinoline
• CAS: 455955-26-7
• 化学式: C₉H₅ClIN
• 分子量: 289.503
• InChiKey: DDDRGSCRLDBUOU-UHFFFAOYSA-N

物化性质

• 沸点：
  349.3±22.0 °C(Predicted)
• 密度：
  1.919±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-5-iodoquinoline 在 硫酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 5-iodo-2-(piperazin-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
• 作为产物：
  描述：

  3-碘苯胺 在 吡啶 、 硫酸 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 2-chloro-5-iodoquinoline
  参考文献：
  名称：

  从杂化的金属-配体氢键（MLHB）配体亚基中选择一个自组装的大环

  摘要：

  为了扩展自组装金属配体与氢键结构之间的界面，在此我们报告吡啶基喹诺酮配体（5-PYQ）的制备，自组装和金属配体结合。5-PYQ配体通过喹诺酮氢键自缔合，并通过吡啶配体组分与金属中心结合。作为研究更复杂的混合金属-配体氢键（MLHB）体系结构的第一步，我们报告了对具有单-和双-二价键的5-PYQ的研究铂蒽前体。这些结果表明5-PYQ配体在与正方形平面的铂中心结合时保持氢键相互作用，但是具有封闭拓扑结构的配位化合物的生成侵蚀了氢键的保真度，从而有利于5-PYQ配体的双键配位模式。

  DOI：

  10.1021/acs.inorgchem.5b00857

文献信息

• QUINOLINES
  申请人：Kolczewski Sabine

  公开号：US20080146567A1

  公开（公告）日：2008-06-19

  The present invention relates to 2-Aminoquinoline derivatives of general formula I and pharmaceutically-acceptable acid-addition salts thereof, wherein R 1 , R 2 and X are as defined in the specification. The compounds may be used as 5-HT 5A receptor antagonists. The present invention relates also to processes for making such a compound and a pharmaceutical composition comprising such a compound. Compounds of the present invention are useful in the prevention and/or treatment of anxiety depression, anxiety disorders, schizophrenia, panic disorders, agoraphobia, social phobia, obsessive compulsive disorders, post-traumatic stress disorders, pain, memory disorders, dementia, disorders of eating behaviors, sexual dysfunction, sleep disorders, withdrawal from abuse of drugs, motor disorders such as Parkinson's disease, psychiatric disorders and gastrointestinal disorders.

  本发明涉及一般式I的2-氨基喹啉衍生物及其药用可接受的酸盐，其中R1、R2和X如规范中所定义。这些化合物可以用作5-HT5A受体拮抗剂。本发明还涉及制备这种化合物的方法以及包含这种化合物的药物组合物。本发明的化合物在预防和/或治疗焦虑抑郁症、焦虑障碍、精神分裂症、惊恐障碍、广场恐惧症、社交恐惧症、强迫症、创伤后应激障碍、疼痛、记忆障碍、痴呆症、饮食行为障碍、性功能障碍、睡眠障碍、戒除药物滥用、帕金森病等运动障碍、精神障碍和胃肠道障碍方面具有用处。
• 2-AMINOQUINOLINES
  申请人：Kolczewski Sabine

  公开号：US20090227628A1

  公开（公告）日：2009-09-10

  The present invention is concerned with 2-aminoquinoline derivatives of formula I wherein Z, R1, and Ar1 are as defined herein, pharmaceutical compositions containing them, methods for their manufacture. The compounds are 5-HT 5A receptor antagonists and are useful in the prevention and/or treatment of depression, anxiety disorders, schizophrenia, panic disorders, agoraphobia, social phobia, obsessive compulsive disorders, post-traumatic stress disorders, pain, memory disorders, dementia, disorders of eating behaviors, sexual dysfunction, sleep disorders, abuse of drugs, motor disorders such as Parkinson's disease, psychiatric disorders or gastrointestinal disorders.

  本发明涉及公式I的2-氨基喹啉衍生物，其中Z、R1和Ar1的定义如本文所述，以及含有它们的药物组合物、其制造方法。这些化合物是5-HT5A受体拮抗剂，可用于预防和/或治疗抑郁症、焦虑障碍、精神分裂症、惊恐障碍、广场恐惧症、社交恐惧症、强迫症、创伤后应激障碍、疼痛、记忆障碍、痴呆、进食行为障碍、性功能障碍、睡眠障碍、药物滥用、帕金森病等运动障碍、精神障碍或胃肠道障碍的治疗。
• 2-AMINOQUINOLINE DERIVATIVES
  申请人：Kolczewski Sabine

  公开号：US20090227584A1

  公开（公告）日：2009-09-10

  The present invention is concerned with 2-aminoquinoline derivatives, in particular compounds of formula (I) wherein R 1 and R 2 are as described herein, pharmaceutical compositions containing such compounds, and methods for their manufacture. The compounds of the invention are 5-HT 5A receptor antagonists useful in the prevention and/or treatment of depression, anxiety disorders, schizophrenia, panic disorders, agoraphobia, social phobia, obsessive compulsive disorders, post-traumatic stress disorders, pain, memory disorders, dementia, disorders of eating behaviors, sexual dysfunction, sleep disorders, abuse of drugs, motor disorders such as Parkinson's disease, psychiatric disorders or gastrointestinal disorders.

  本发明涉及2-氨基喹啉衍生物，特别是具有式(I)的化合物，其中R1和R2如本文所述，含有这种化合物的药物组合物，以及它们的制备方法。本发明的化合物是5-HT5A受体拮抗剂，在预防和/或治疗抑郁症、焦虑障碍、精神分裂症、恐慌障碍、广场恐惧症、社交恐惧症、强迫性障碍、创伤后应激障碍、疼痛、记忆障碍、痴呆、进食行为障碍、性功能障碍、睡眠障碍、药物滥用、帕金森病等运动障碍、精神障碍或胃肠道障碍的预防和/或治疗中有用。
• II. Synthesis and Biological Evaluation of Some Bioisosteres and Congeners of the Antitumor Agent, 2-{4-[(7-Chloro-2-quinoxalinyl)oxy]phenoxy}propionic Acid (XK469)
  作者：Stuart T. Hazeldine、Lisa Polin、Juiwanna Kushner、Kathryn White、Nicole M. Bouregeois、Brianna Crantz、Eduardo Palomino、Thomas H. Corbett、Jerome P. Horwitz

  DOI：10.1021/jm0200097

  日期：2002.7.1

  (21a-g) ring systems. The synthetic approach to each of the bioisosteres of 1 utilized the methodology developed in previous work (see Hazeldine, S. T.; Polin, L.; Kushner, J.; Paluch, J.; White, K.; Edelstein, M.; Palomino, E.; Corbett, T. H.; Horwitz, J. P. Design, Synthesis, and Biological Evaluation of Analogues of the Antitumor Agent 2-(4-[(7-Chloro-2-quinoxalinyl)oxy]phenoxy)propionic acid (XK469)

  XK469（1）是我们实验室中评估的最高度和最广泛活性的抗肿瘤药物之一。随后的开发研究导致（R）-（+）1（NSC 698215）进入1期临床试验（NIH UO1-CA62487）。1的抗肿瘤作用机理尚待阐明，这促使人们不断努力拟订1的药效学模式。本研究的重点是对喹喔啉部分中基于拓扑的生物等位替代物进行合成和生物学评估的策略。铅化合物（1）由喹唑啉（4a-d），1,2,4-苯并三嗪（12a-18b）和喹啉（21a-g）环系统合成。对每个1的生物等排体的合成方法都采用了先前工作中开发的方法（请参见ST的Hazeldine； L。的Polin； J。的Kushner； J。的Paluch； J。的White； K.EdelSTein； M。的Palomino，E .; TH，Corbett；Horwitz，JP设计，合成和抗肿瘤药2-（4-[（7-氯-2-喹喔啉基）氧基]苯氧基）丙酸（XK469）类似物的生物学评估。J
• QUINOLINE DERIVATIVES FOR INHIBITING HISTONE METHYLTRANSFERASES AND USE THEREOF
  申请人：KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY

  公开号：US20170354650A1

  公开（公告）日：2017-12-14

  The present disclosure relates to a quinoline derivative which inhibits the activity of histone methyltransferases (ESET/SETDB1) specific for the histone molecule H3K9 or a pharmaceutically acceptable salt thereof and a use thereof.

  本公开涉及一种喹啉衍生物，其抑制特定于组蛋白分子H3K9的组蛋白甲基转移酶（ESET/SETDB1）的活性或其药用盐，以及其用途。