2-chloro-3-(4-methoxyphenyl)quinoline | 85274-80-2

• 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: 2-chloro-3-(4-methoxyphenyl)quinoline
• CAS: 85274-80-2
• 化学式: C₁₆H₁₂ClNO
• 分子量: 269.73
• InChiKey: GDPLCCRQIHQGOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-chloro-3-(4-methoxyphenyl)quinoline 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 1-ethyl-4-(4-methoxyphenyl)-[1,2,4]triazolo[4,3-a]quinoline
  参考文献：
  名称：

  作为亲电子试剂的硝基烷烃：具有神经母细胞瘤分化活性的三唑稠合杂环化合物的合成。

  摘要：

  我们发现了硝基烷烃与 2-肼基喹啉、2-肼基吡啶和双 2,4-二肼基嘧啶在多磷酸 (PPA) 中的反应，得到 1,2,4-三唑并[4,3- a ]喹啉, 1,2,4 -三唑并[4,3- a ]吡啶和双[1,2,4]三唑并[4,3- a :4′,3′- c]嘧啶，分别。该反应扩大了涉及磷酸化硝酸盐的杂环环化的范围，被认为是由 PPA 中的硝基烷形成的亲电子中间体。几种合成的三唑类化合物通过诱导神经母细胞瘤癌细胞分化而显示出有希望的抗癌活性。由于迫切需要用于神经母细胞瘤治疗的新型分化剂，这一发现值得进一步评估这类化合物对神经母细胞瘤的治疗作用。

  DOI：

  10.1039/d0ob01007c
• 作为产物：
  描述：

  N-(2-((4-methoxyphenyl)ethynyl)phenyl)formamide 在 N,N-二异丙基乙胺 、 三氯氧磷 、 四丁基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以97%的产率得到2-chloro-3-(4-methoxyphenyl)quinoline
  参考文献：
  名称：

  Tetrabutylammonium chloride-triggered 6-endo cyclization of o-alkynylisocyanobenzenes: an efficient synthesis of 2-chloro-3-substituted quinolines

  摘要：

  A highly efficient one-pot synthesis of 2-chloro-3-substituted quinolines has been developed by tetrabutylammonium chloride-triggered 6-endo cyclization of o-alkynylisocyanobenzenes, which are generated in situ by dehydration of the corresponding N-(2-ethynylphenyl)formamides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.096

文献信息

• Synthesis of 4-Aryl-2-aminopyridine Derivatives and Related Compounds
  作者：Vladimir Pavlovic、Milos Petkovic、Stanimir Popovic、Vladimir Savic

  DOI：10.1080/00397910902898601

  日期：2009.11.5

  Abstract A short, efficient, and high-yielding synthesis of 4-aryl-2-aminopyridine derivatives has been developed. The route employs two palladium-catalyzed processes, the Suzuki reaction and the Buchwald–Hartwig amination, as the key steps. The same approach has been used for preparation of the corresponding quinoline derivatives. In addition, a brief study of biological properties showed the anticancer

  摘要 4-芳基-2-氨基吡啶衍生物的快速、高效、高产合成已被开发。该路线采用两个钯催化过程，铃木反应和 Buchwald-Hartwig 胺化，作为关键步骤。相同的方法已用于制备相应的喹啉衍生物。此外，对生物学特性的简要研究显示了这些化合物的抗癌潜力。
• ISOINDOLINE PDE10 INHIBITORS
  申请人：Bunda Jamie L.

  公开号：US20130203756A1

  公开（公告）日：2013-08-08

  The present invention is directed to isoindolinone compounds which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 10 (PDE10). 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isoindolinone化合物，其可用作治疗与磷酸二酯酶10（PDE10）相关的中枢神经系统疾病的治疗剂。本发明还涉及使用这些化合物治疗神经系统和精神疾病，如精神分裂症、精神病或亨廷顿病，以及与纹状体功能减退或基底节功能障碍有关的疾病。
• Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogs
  作者：Thomas P. Blackburn、Barry Cox、Allen J. Guildford、David J. Le Count、Derek N. Middlemiss、Robert J. Pearce、Craig W. Thornber

  DOI：10.1021/jm00395a013

  日期：1987.12

  A series of 2-[(2-aminoethyl)thio]quinolines substituted at the 3-position with alkyl, aryl, or heteroaryl groups has been prepared in the search for novel and selective 5-HT2 antagonists. The affinity of the compounds for 5-HT1 receptor sites was measured by their ability to displace [3H]-5-HT from rat brain synaptosomes whereas the affinity for 5-HT2 receptor sites was measured by their ability to displace [3H]spiperone from synaptosomes prepared from rat brain cortex. The 5-HT2 antagonist properties of the compounds were measured in vivo by their antagonism of 5-hydroxytryptophan-induced head twitches in the mouse and by their antagonism of hyperthermia induced by fenfluramine (N-ethyl-alpha-methyl-m-(trifluoromethyl)phenethylamine hydrochloride) in the rat. The structure-activity relationships in this series are discussed and the properties of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline hydrochloride (70) are highlighted.
• BLACKBURN, THOMAS P.;COX, BARRY;GUILDFORD, ALLEN J.;LE, COUNT DAVID J.;MI+, J. MED. CHEM., 30,(1987) N 12, 2252-2259
  作者：BLACKBURN, THOMAS P.、COX, BARRY、GUILDFORD, ALLEN J.、LE, COUNT DAVID J.、MI+

  DOI：——

  日期：——
• ISOINDOLINONE PDE10 INHIBITORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2632461A1

  公开（公告）日：2013-09-04