2-氯-4-甲基-3-苯基喹啉 | 89081-06-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 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
• 中文名称: 2-氯-4-甲基-3-苯基喹啉
• 英文名称: 2-chloro-4-methyl-3-phenylquinoline
• CAS: 89081-06-1
• 化学式: C₁₆H₁₂ClN
• 分子量: 253.731
• InChiKey: DYSUHDOSVZCJEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-甲胺乙硫醇盐酸盐 、 2-氯-4-甲基-3-苯基喹啉 在 sodium hydride 作用下， 生成 Dimethyl-[2-(4-methyl-3-phenyl-quinolin-2-ylsulfanyl)-ethyl]-amine
  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：

  2'-acetyl-1-phenylacetanilide 在 sodium 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 2-氯-4-甲基-3-苯基喹啉
  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

文献信息

• [EN] QUINOLINE DERIVATIVES AND USE THEREOF AS MYCOBACTERIAL INHIBITORS<br/>[FR] DERIVES DE QUINOLINE ET UTILISATION DE CEUX-CI EN TANT QU'INHIBITEURS MYCOBACTERIENS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2005070430A1

  公开（公告）日：2005-08-04

  The present invention relates to novel substituted quinoline derivatives according to the general Formula (Ia) or the general Formula (Ib) the pharmaceutically acceptable acid or base addition salts thereof, the quaternary amines thereof, the stereochemically isomeric forms thereof, the tautomeric forms thereof and the N-oxide forms thereof. The claimed compounds are useful for the treatment of mycobacterial diseases.

  本发明涉及根据一般式(Ia)或一般式(Ib)的新型取代喹啉衍生物，其药学上可接受的酸或碱盐，其季铵盐，其立体化异构体形式，其互变异构体形式和其N-氧化物形式。所述化合物可用于治疗分枝杆菌病。
• Quinoline derivatives which are 5-hydroxytryptamine antagonists
  申请人：Imperial Chemical Industries PLC

  公开号：US04607039A1

  公开（公告）日：1986-08-19

  Compounds of the formula: ##STR1## wherein A stands for the radical --(CH.sub.2).sub.2 -- which may optionally be substituted by one or two (1-2C)alkyl radicals; Q stands for an oxygen or sulphur atom; R.degree. stands for a (1-4C)alkyl, (1-4C)alkoxy or cyclopropyl radical; R.sup.1 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 or 6 ring atoms; and R.sup.2 and R.sup.3 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 carrier. The compounds are 5-hydroxytryptamine antagonists.

  该公式化合物为：##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代表定义的(3-4C)烷基基团，一个苯基基团，该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盐。制造这些化合物的方法。包括其中一种化合物和药用稀释剂或载体的药物组合物。这些化合物是5-羟色胺拮抗剂。
• [EN] QUINOLINE DERIVATIVES AS P13 KINASE INHIBITORS<br/>[FR] DÉRIVÉS DE QUINOLÉINE EN TANT QU'INHIBITEURS DE PI3-KINASE
  申请人：UCB PHARMA SA

  公开号：WO2010061180A1

  公开（公告）日：2010-06-03

  A series of quinoline derivatives, substituted at the 2-position by a heteroaryl group attached via an alkylene chain optionally linked to a heteroatom, and at the 3-position by a carbocyclic or heterocylic ring, being selective inhibitors of PD kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列喹啉衍生物，在2-位置被通过烷基链连接到杂环芳基团上取代，并在3-位置被碳环或杂环环取代，是选择性PD激酶酶抑制剂，在医学上具有益处，例如用于治疗炎症、自身免疫、心血管、神经退行性、代谢、肿瘤、疼痛或眼科疾病。
• 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。
• [EN] QUINOLINE DERIVATIVES AS ANTIBACTERICAL AGENTS<br/>[FR] DERIVES DE QUINOLEINE UTILISES COMME AGENTS ANTIBACTERIENS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2007014940A3

  公开（公告）日：2007-03-29