4-phenyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile | 16560-18-2

• 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: 4-phenyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile
• 英文别名: 2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carbonitrile；1,2-dihydro-2-oxo-4-phenyl-3-quinolinecarbonitrile；3-Cyan-4-phenyl-carbostyril；4-Phenyl-3-cyan-carbostyril；2-oxo-4-phenyl-1H-quinoline-3-carbonitrile
• CAS: 16560-18-2
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: GKYGZXCLSZLRPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile 在 sodium hydride 、 sodium iodide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 1-[3-(dimethylamino)propyl]-1,2-dihydro-2-oxo-4-phenyl-3-quinolinecarbonitrile
  参考文献：
  名称：

  Discovery of a novel series of quinolone α7 nicotinic acetylcholine receptor agonists

  摘要：

  High throughput screening led to the identification of a novel series of quinolone alpha 7 nicotinic acetylcholine receptor (nAChR) agonists. Optimization of an HTS hit (1) led to 4-phenyl-1-(quinuclidin-3-ylmethyl)quinolin-2(1H)-one, which was found to be potent and selective. Poor brain penetrance in this series was attributed to transporter-mediated efflux, which was in turn due to high pK(a). A novel 4-fluoroquinuclidine significantly lowered the pK(a) of the quinuclidine moiety, reducing efflux as measured by a Caco-2 assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.070
• 作为产物：
  描述：

  2,4-二氯喹啉-3-甲腈 在 二(三叔丁基膦)钯 、 水 、 caesium carbonate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 4-phenyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile
  参考文献：
  名称：

  [EN] PHENYL-CYANOQUINOLINONE PDE9 INHIBITORS
  [FR] PHÉNYLCYANOQUINOLINONES UTILES EN TANT QU'INHIBITEURS DE PDE9

  摘要：

  本发明涉及苯基氰基喹诺酮化合物，可能作为治疗与磷酸二酯酶9（PDE9）相关的中枢神经系统疾病的治疗剂。本发明还涉及利用这些化合物治疗神经学和精神疾病，如精神分裂症、精神病或亨廷顿病，以及与纹状体功能不足或基底神经节功能障碍相关的疾病。

  公开号：

  WO2017019724A1

文献信息

• Substituted coumarins and quinolines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cytovia, Inc.

  公开号：US20030114485A1

  公开（公告）日：2003-06-19

  The present invention is directed to substituted coumarins and quinolines and analogs thereof, represented by the general Formula I: 1 wherein A, B, X, Y, and Z are defined herein. The present invention also relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及取代香豆素和喹啉及其类似物，由一般式I：1表示，其中A、B、X、Y和Z在此处定义。本发明还涉及发现具有式I的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在出现异常细胞的不受控制的生长和传播的各种临床状况中的细胞死亡。
• 1,2-Dihydro-2-oxo-4-phenyl-3-quinolinecarbonitrile derivatives
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04232027A1

  公开（公告）日：1980-11-04

  1,2-Dihydro-2-oxo-4-phenyl-3-quinolinecarbonitrile derivatives are provided having the structure ##STR1## wherein (CH.sub.2).sub.n represents a straight chain alkylene group containing 2 to 5 carbons, and R.sub.1 and R.sub.2 are the same or different and may be hydrogen or lower alkyl with the proviso that at least one of R.sub.1 and R.sub.2 is lower alkyl, or ##STR2## can be taken together to form a heterocyclic radical containing 5- or 6-members in the heterocyclic ring, such as pyrrolidino, piperidino or morpholino, and R.sub.3 and R.sub.4 may be the same or different and are hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl, and physiologically acceptable acid addition salts thereof. These compounds are useful as anti-inflammatory agents. A pharmaceutical composition containing the above compounds and a method of use are also provided.

  提供了具有以下结构的1,2-二氢-2-氧代-4-苯基-3-喹啉羧腈衍生物##STR1##其中(CH.sub.2).sub.n代表含有2到5个碳的直链烷基，R.sub.1和R.sub.2相同或不同，可以是氢或较低的烷基，但至少有一个R.sub.1和R.sub.2是较低的烷基，或者##STR2##可以结合成含有5-或6-成员的杂环基，例如吡咯烷基，哌啶基或吗啡啉基，R.sub.3和R.sub.4可以相同或不同，可以是氢，较低的烷基，较低的烷氧基，卤素或三氟甲基，以及其生理学上可接受的酸盐。这些化合物可用作抗炎剂。还提供了包含上述化合物的制药组合物和使用方法。
• Quinoline potassium channel inhibitors
  申请人：Dinsmore J. Christopher

  公开号：US20070078154A1

  公开（公告）日：2007-04-05

  The present invention relates to compounds having the structure (I) useful as potassium channel inhibitors to treat cardiac arrhythmias, and the like.

  本发明涉及具有结构式（I）的化合物，其作为钾通道抑制剂用于治疗心律失常等。
• Phenyl-cyanoquinolinone PDE9 inhibitors
  申请人：Merck Sharp & Dohme Corp.

  公开号：US10370336B2

  公开（公告）日：2019-08-06

  The present invention is directed to phenylcyanoquinolinone compounds which may be useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 9 (PDE9). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

  本发明涉及苯基氰基喹啉酮化合物，该化合物可作为治疗剂用于治疗与磷酸二酯酶9（PDE9）相关的中枢神经系统疾病。本发明还涉及使用此类化合物治疗神经和精神疾病，如精神分裂症、精神病或亨廷顿氏病，以及与纹状体功能低下或基底节功能障碍相关的疾病。
• TiO₂ Nanopowder Catalyzed Microwave-Induced One-Pot Synthesis of Novel Quinoline/Benzo[<i>h</i>]quinoline3-carbonitrile Under Solvent Free Conditions
  作者：H. R. Prakash Naik、H. S. Bhojya Naik、T. R. Ravikumar Naik、T. Aravinda、D. S. Lamani

  DOI：10.1080/10426500802424048

  日期：2009.8.6

  A rapid and efficient method for the synthesis of various carbonitrile quinoline/benzo[h]quinolines has been developed through the Knoevenagel condensation, Michael addition of aromatic aldehyde/amine with carbonyl compounds in the presence of a nanostructured TiO2 photocatalyst by microwave irradiation under solvent-free conditions.