5-(2-Bromoethoxy)-7-chloro-2-methylquinoline | 420786-74-9

• 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: 5-(2-Bromoethoxy)-7-chloro-2-methylquinoline
• CAS: 420786-74-9
• 化学式: C₁₂H₁₁BrClNO
• 分子量: 300.582
• InChiKey: MMISOJYOTXXBDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-methyl-8-(piperidin-4-ylmethyl)4H-benzo[1,4]oxazin-3-one 、 5-(2-Bromoethoxy)-7-chloro-2-methylquinoline 生成 8-{1-[2-(7-Chloro-2-methylquinolin-5-yloxy)ethyl]piperidin-4-ylmethyl}-4-methyl-4H-benzo[1,4]oxazin-3-one
  参考文献：
  名称：

  Heterocyclymethylpiperidines and -piperazines possessing affinity at 5ht-1 type receptors

  摘要：

  公开了式（I）的化合物及其药学上可接受的盐： 其中：A是可选取代的苯基，萘基，吲哚基，喹啉基，喹唑啉基，吲唑基，异喹啉基或苯并呋喃基；X是碳，Y是CH，且为双键；或X是CH，Y是CH2或氧，且为单键；或X是氮，Y是CH2，且为单键；R1是卤素，氰基或C1-6烷氧基；a为0、1、2或3；b为0或1；R2是氢，C1-6烷基，C1-6烷酰基，氟代C1-6烷酰基，C1-6烷基磺酰基，氟代C1-6烷基磺酰基，氨基甲酰基，C1-6烷基氨基甲酰基或芳基C1-6烷基；以及R3与其连接的氮原子一起形成一个可选取代的5到7成员杂环基固定在苯环上。还公开了制备这些化合物的方法以及这些化合物在治疗中的应用，特别是用于中枢神经系统紊乱，如抑郁症或焦虑症。

  公开号：

  US07214674B2
• 作为产物：
  描述：

  5,7-二氯-2-甲基喹啉 在 三溴化硼 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丁酮 为溶剂， 生成 5-(2-Bromoethoxy)-7-chloro-2-methylquinoline
  参考文献：
  名称：

  3,4-Dihydro-2H-benzoxazinones as dual-acting 5-HT1A receptor antagonists and serotonin reuptake inhibitors

  摘要：

  Investigation of halogen substitution in lead compound 1 has led to the identification of analogues which combine high affinity for 5-HT1A receptors and potent serotonin reuptake inhibitory activity. Several compounds show an improved selectivity over 5-HT1B and 5-HT1D receptors and a superior pharmacokinetic profile in the rat. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.031

文献信息

• HETEROCYCLYLMETHYLPIPERIDINES AND -PIPERAZINES POSSESSING AFFINITY AT 5HT-1 TYPE RECEPTORS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1480974A1

  公开（公告）日：2004-12-01
• US7214674B2
  申请人：——

  公开号：US7214674B2

  公开（公告）日：2007-05-08
• [EN] HETEROCYCLYMETHYLPIPERIDINES AND -PIPERAZINES POSSESSING AFFINITY AT 5HT-1 TYPE RECEPTORS<br/>[FR] HETEROCYCLYL-METHYLPIPERIDINES ET HETEROCYCLYL-METHYLPIPERAZINES POSSEDANT UNE AFFINITE AVEC DES RECEPTEURS DU TYPE 5HT-1
  申请人：GLAXO GROUP LTD

  公开号：WO2003068771A1

  公开（公告）日：2003-08-21

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed, wherein: A is optionally substituted phenyl, naphthyl, indolyl, quinolinyl, quinazolinyl, indazolyl, isoquinolinyl or benzofuranyl; X is carbon, Y is CH and === is a double bond; or X is CH, Y is CH2 or oxygen and === is a single bond; or X is nitrogen, Y is CH2 And === is a single bond; R1is halogen, cyano, or C1-6 alkoxy; a is 0, 1, 2 or 3; b is 0 or 1; R2 is hydrogen, C1-6 alkyl, C1-6 alkanoyl, fluoroC1-6 alkanoyl, C1-6 alkylsulfonyl, fluoroC1-6 alkylsulfonyl, carbamoyl, C1-6 alkylcarbamoyl or arylC1-6 alkyl; and R3, together with the nitrogen atom to which it is attached, forms an optionally substituted 5 to 7 membered heterocyclic group fused to the benzene ring. Methods of preparing the compounds and uses of the compounds in therapy, in particular for a CNS disorder such as depression or anxiety, are also disclosed.
• 3,4-Dihydro-2H-benzoxazinones as dual-acting 5-HT1A receptor antagonists and serotonin reuptake inhibitors
  作者：Peter J. Lovell、Frank E. Blaney、Caroline J. Goodacre、Claire M. Scott、Paul W. Smith、Kathryn R. Starr、Kevin M. Thewlis、Antonio K.K. Vong、Simon E. Ward、Jeannette M. Watson

  DOI：10.1016/j.bmcl.2006.11.031

  日期：2007.2

  Investigation of halogen substitution in lead compound 1 has led to the identification of analogues which combine high affinity for 5-HT1A receptors and potent serotonin reuptake inhibitory activity. Several compounds show an improved selectivity over 5-HT1B and 5-HT1D receptors and a superior pharmacokinetic profile in the rat. (c) 2006 Elsevier Ltd. All rights reserved.
• Heterocyclymethylpiperidines and -piperazines possessing affinity at 5ht-1 type receptors
  申请人：Ward E. Simon

  公开号：US20050153974A1

  公开（公告）日：2005-07-14

  Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed: wherein: A is optionally substituted phenyl, naphthyl, indolyl, quinolinyl, quinazolinyl, indazolyl, isoquinolinyl or benzofuranyl; X is carbon, Y is CH and is a double bond; or X is CH, Y is CH 2 or oxygen and is a single bond; or X is nitrogen, Y is CH 2 and is a single bond; R1 is halogen, cyano, or C 1-6 alkoxy; a is 0, 1, 2 or 3; b is 0 or 1; R2 is hydrogen, C 1-6 alkyl, C 1-6 alkanoyl, fluoroC 1-6 alkanoyl, C 1-6 alkylsulfonyl, fluoroC 1-6 alkylsulfonyl, carbamoyl, C 1-6 alkylcarbamoyl or arylC 1-6 alkyl; and R3, together with the nitrogen atom to which it is attached, forms an optionally substituted 5 to 7 membered heterocyclic group fused to the benzene ring. Methods of preparing the compounds and uses of the compounds in therapy, in particular for a CNS disorder such as depression or anxiety, are also disclosed.

  公开了化学式（I）的化合物及其药用可接受的盐：其中：A是可选取代的苯基、萘基、吲哚基、喹啉基、喹唑啉基、吲唑基、异喹啉基或苯并呋喃基；X是碳，Y是CH且是双键；或X是CH，Y是CH2或氧且是单键；或X是氮，Y是CH2且是单键；R1是卤素、氰基或C1-6烷氧基；a为0、1、2或3；b为0或1；R2是氢、C1-6烷基、C1-6酰基、氟代C1-6酰基、C1-6烷基磺酰基、氟代C1-6烷基磺酰基、氨基甲酰基、C1-6烷基氨基甲酰基或芳基C1-6烷基；R3与其连接的氮原子一起形成一个可选取代的5到7元杂环基固定在苯环上。还公开了制备该化合物的方法以及该化合物在治疗中的用途，特别是用于中枢神经系统紊乱如抑郁症或焦虑症。