4-chloro-3-methyl-quinoline-2(1H)-one | 56857-98-8

• 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-chloro-3-methyl-quinoline-2(1H)-one
• 英文别名: 4-chloro-3-methylquinolin-2(1H)-one；4-chloro-3-methyl-1H-quinolin-2-one；4-Chlor-3-methyl-2-chinolon；4-chloro-3-methyl-1H-quinolin-2-one
• CAS: 56857-98-8
• 化学式: C₁₀H₈ClNO
• mdl: MFCD05666223
• 分子量: 193.633
• InChiKey: DIXWCKMHYAWPEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chloro-3-methyl-quinoline-2(1H)-one 、 4-乙基苯硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 4-(4-ethylphenyl)-3-methylquinolin-2(1H)-one
  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
• 作为产物：
  描述：

  2,4-二氯-3-甲基喹啉 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 以93%的产率得到4-chloro-3-methyl-quinoline-2(1H)-one
  参考文献：
  名称：

  Nucleophilic Chlorination of 3-Formyl-4-hydroxy-quinolin-2(1H)-ones

  摘要：

  Chlorination of 1-substituted 3-formyl-4-hydroxy-2-quinolones (1a, b) with phosphorylchloride leads to 4-chloro-3-dichloromethylquinolones (2), which can be hydrolyzed to 4-chloro-3-formylquinolones (4). From the anilinomethylene quinolinediones (3), at low temperatures the formylquinolones 4 can be obtained directly, whereas at high temperatures cleavage of the tautomeric azomethine moiety followed by subsequent ring closure to the naphthyridines (7) takes place. With 1-unsubstituted 3-formyl-4-hydroxy-2-quinolones (1d) either the 3-dichloromethylquinolone (2d) or the 2,4-dichloro-3-dichloromethylquinoline (10) is obtained depending on the reaction conditions. Similar results are obtained with the 1-unsubstituted anilinomethylene compounds (3). Attempts to obtain the 3-formyl-2,4-dichloroquinoline (11) were unsuccessful because in all experiments the 2-chloro-group was converted to an oxygen function.

  DOI：

  10.1002/prac.19933350203

文献信息

• Certain substituted quinolones, compositions, and uses thereof
  申请人：Dickson K. John

  公开号：US20070287706A1

  公开（公告）日：2007-12-13

  Certain quinolone-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, methods of using compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions comprising compounds exhibiting ATP-utilizing enzyme inhibitory activity, are disclosed.

  揭示了具有ATP利用酶抑制活性的某些喹诺酮基化合物，以及使用具有ATP利用酶抑制活性的化合物的方法和包含具有ATP利用酶抑制活性的化合物的组合物。
• 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。
• AHLBRECHT H.; VONDERHEID C., CHEM. BER. <CHBE-AM>, 1975, 108, NO 7, 2300-2311
  作者：AHLBRECHT H.、 VONDERHEID C.

  DOI：——

  日期：——
• PHENYL-CYANOQUINOLINONE PDE9 INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20180208557A1

  公开（公告）日：2018-07-26

  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.