2,4-Dimethoxy-3-o-tolyl-quinoline | 89080-82-0

• 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: 2,4-Dimethoxy-3-o-tolyl-quinoline
• 英文别名: 2,4-Dimethoxy-3-(2-methylphenyl)quinoline
• CAS: 89080-82-0
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: SJFHLJHMEGDQLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-Dimethoxy-3-o-tolyl-quinoline 在 盐酸 作用下， 反应 2.0h， 生成 4-methoxy-3-o-tolylquinolin-2-one
  参考文献：
  名称：

  Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogs

  摘要：

  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.

  DOI：

  10.1021/jm00395a013
• 作为产物：
  描述：

  sodium methylate 、 2,4-dichloro-3-(2-methylphenyl)quinoline 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2,4-Dimethoxy-3-o-tolyl-quinoline
  参考文献：
  名称：

  Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogs

  摘要：

  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.

  DOI：

  10.1021/jm00395a013
• 作为试剂：
  描述：

  2,4-dichloro-3-(2-methylphenyl)quinoline 、 sodium methylate 、 水 在 乙酸乙酯 、 水 、 magnesium sulfate 、 2,4-Dimethoxy-3-o-tolyl-quinoline 、 盐酸 、 ethyl acetate-petroleum ether 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以to give 4-methoxy-3-o-tolylquinolin-2-one, m.p. 215°的产率得到4-methoxy-3-o-tolylquinolin-2-one
  参考文献：
  名称：

  Quinoline derivatives which are 5-hydroxytryptamine antagonists

  摘要：

  化合物的公式为：## STR1 ## 其中A代表基团 - (CH.sub.2) .sub.2-，可以选择性地被一个或两个（1-2C）烷基基团取代; Q代表氧或硫原子; R.degree.代表（1-4C）烷基，（1-4C）烷氧基或环丙基基团; R.sup.1代表一个定义的（3-4C）烷基基团，一个苯基基团，可以选择性地带有一个定义的取代基，或者一个由5个或6个环原子组成的定义的杂环基团; R.sup.2和R.sup.3代表氢或（1-2C）烷基基团;以及其药学上可接受的酸加合盐。制造该化合物的过程。包含其中一种化合物和药用稀释剂或载体的制药组合物。这些化合物是5-羟色胺拮抗剂。

  公开号：

  US04607039A1

文献信息

• Quinoline derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0093521A2

  公开（公告）日：1983-11-09

  Compounds of the formula:- wherein A stands for the radical -(CH2)2- which may optionally be substituted by one or two (1-2C)alkyl radicals; Q stands for an oxygen or sulphur atom; R° stands for a (1-4C)alkyl, (1-4C)alkoxy or cyclopropyl radical; R' stands for a defined (3-4C)alkyl radical, a phenyl radical which may optionally bear a defined substituent, or a defined heteroaryl radical of 5 to 6 ring atoms; and R2 and R3 stand for hydrogen or a (1-2C)alkyl radical; and pharmaceutically-acceptable acid-addition salts thereof. Processes for the manufacture of said compounds. Pharmaceutical compositions comprising one of said compounds and a pharmaceutical diluent or cerrier. The compounds are 5-hydroxytryptamine antagonists.

  式中化合物 其中 A 代表自由基-(CH2)2-，可任选被一个或两个(1-2C)烷基取代；Q 代表氧原子或硫原子；R° 代表(1-4C)烷基、(1-4C)烷氧基或环丙基；R'代表定义的(3-4C)烷基、可任选带有定义取代基的苯基或 5 至 6 个环原子的定义杂芳基；以及 R2 和 R3 代表氢或(1-2C)烷基；及其药学上可接受的酸加成盐。上述化合物的生产工艺。包含上述化合物之一和药用稀释剂或陶瓷载体的药用组合物。所述化合物是5-羟色胺拮抗剂。
• US4607039A
  申请人：——

  公开号：US4607039A

  公开（公告）日：1986-08-19
• 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.