4-Chloro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)quinoline | 332181-90-5

• 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-2-(1,2,3,4-tetrahydronaphthalen-2-yl)quinoline
• CAS: 332181-90-5
• 化学式: C₁₉H₁₆ClN
• 分子量: 293.796
• InChiKey: SRVXIKUVPAOPMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  3-氨基-1,2-丙二醇 、 4-Chloro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)quinoline 生成 3-[[2-(1,2,3,4-Tetrahydronaphthalen-2-yl)quinolin-4-yl]amino]propane-1,2-diol
  参考文献：
  名称：

  4-Aminoquinolines as a novel class of NR1/2B subtype selective NMDA receptor antagonists

  摘要：

  Screening of the Roche compound library led to the identification of 4-aminoquinoline 4 as structurally novel NR1/2B subtype selective NMDA receptor antagonist. The SAR which was developed in this series resulted in the discovery of highly potent and in vivo active blockers. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00470-5
• 作为产物：
  描述：

  (RS)-2-(1,2,3,4-tetrahydro-naphthalen-2-yl)-1H-quinolin-4-one 在 三氯氧磷 作用下， 以64%的产率得到4-Chloro-2-(1,2,3,4-tetrahydronaphthalen-2-yl)quinoline
  参考文献：
  名称：

  4-Aminoquinolines as a novel class of NR1/2B subtype selective NMDA receptor antagonists

  摘要：

  Screening of the Roche compound library led to the identification of 4-aminoquinoline 4 as structurally novel NR1/2B subtype selective NMDA receptor antagonist. The SAR which was developed in this series resulted in the discovery of highly potent and in vivo active blockers. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00470-5

文献信息

• Quinolin-4-yl derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1088818A1

  公开（公告）日：2001-04-04

  The invention relates to compounds of formula wherein R1is hydrogen, lower alkyl, lower alkoxy, hydroxy, amino, nitro, cyano, lower alkyl-amino, di-lower alkyl-amino or halogen; R2is phenyl, optionally substituted by lower alkyl, lower alkoxy, halogen, trifluoromethyl, amino, lower alkyl-amino or di-lower alkyl-amino 2,3 -dihydro-benzofuran-5-yl, chroman-6-yl, naphthalen-2-yl, indan-5-yl, lower alkenyl-phenyl, 5,6,7,8-tetrahydro-naphthalenyl, 2,3-dihydro-isoindol-2-yl, 1,2,3,4-tetrahydro-naphthalenyl, benzofuran-2-yl, benzo[b]thiophen-2-yl, lower alkyl-phenyl, 3,4-dihydro-1H-isoquinolin-2-yl or thiophen-3-yl; R3 and R4are independently from each other hydrogen or lower alkyl; R5is hydrogen, lower alkyl, -CH2OH or -CH2NR6R7; R6 and R7are independently from each other hydrogen, lower alkyl, - (CH2)n-phenyl, cycloalkyl, -(CH2)m-morpholinyl or form together with the N-atom a saturated ring with 4-6 C-atoms; nis 0-3; mis 2 or 3; Xis -NR8- or -O-; or X and R5are together >N(CH2)2-; or X and R3are together >N(CH2)3-; and R8is hydrogen or lower alkyl; and to pharmaceutically acceptable acid addition salts thereof, with the exception of the following compounds (6-chloro-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol; (6-methyl-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol; (6-methoxy-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol; and (8-methoxy-2-phenyl-4-quinolinyl)-(+)-2-aminobutanol, which may be used for the treatment of diseases, which relate to the NMDA receptor specific blockers.

  本发明涉及如下式的化合物 式中 R1为氢、低级烷基、低级烷氧基、羟基、氨基、硝基、氰基、低级烷基氨基、二低级烷基氨基或卤素； R2是苯基，可选择被低级烷基、低级烷氧基、卤素、三氟甲基、氨基、低级烷基氨基或二低级烷基氨基取代 2,3-二氢-苯并呋喃-5-基、色原-6-基、萘-2-基、茚-5-基、低级烯基-苯基、5,6,7,8-四氢-萘基、2,3-二氢-异吲哚-2-基、1,2,3,4-四氢-萘基、苯并呋喃-2-基、苯并[b]噻吩-2-基、低级烷基-苯基、3,4-二氢-1H-异喹啉-2-基或噻吩-3-基； R3 和 R4 互不独立地为氢或低级烷基； R5 为氢、低级烷基、-CH2OH 或 -CH2NR6R7； R6 和 R7 各自独立地为氢、低级烷基、-(CH2)n-苯基、环烷基、-(CH2)m-吗啉基，或与 N 原子一起形成具有 4-6 个 C 原子的饱和环； n 为 0-3； 错 2 或 3； X是-NR8-或-O-；或 X和R5共同>N(CH2)2-；或 X 和 R3 共同 >N(CH2)3-；以及 R8 为氢或低级烷基； 及其药学上可接受的酸加成盐，但以下化合物除外 (6-氯-2-苯基-4-喹啉基)-(+)-2-氨基丁醇； (6-甲基-2-苯基-4-喹啉基)-(+)-2-氨基丁醇； (6-甲氧基-2-苯基-4-喹啉基)-(+)-2-氨基丁醇；和 (8-甲氧基-2-苯基-4-喹啉基)-(+)-2-氨基丁醇，可用于治疗与 NMDA 受体特异性阻断剂有关的疾病。
• US6440995B1
  申请人：——

  公开号：US6440995B1

  公开（公告）日：2002-08-27
• 4-Aminoquinolines as a novel class of NR1/2B subtype selective NMDA receptor antagonists
  作者：Emmanuel Pinard、Alexander Alanine、Anne Bourson、Bernd Büttelmann、Marie-Paule Heitz、Vincent Mutel,a Ramanjit Gill、Gerhard Trube、René Wyler

  DOI：10.1016/s0960-894x(02)00470-5

  日期：2002.9

  Screening of the Roche compound library led to the identification of 4-aminoquinoline 4 as structurally novel NR1/2B subtype selective NMDA receptor antagonist. The SAR which was developed in this series resulted in the discovery of highly potent and in vivo active blockers. (C) 2002 Elsevier Science Ltd. All rights reserved.