N-(2,3-dihydroxypropyl)-2-methyl-4-quinolinamine | 116289-28-2

• 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: N-(2,3-dihydroxypropyl)-2-methyl-4-quinolinamine
• 英文别名: 3-[(2-Methylquinolin-4-yl)amino]propane-1,2-diol
• CAS: 116289-28-2
• 化学式: C₁₃H₁₆N₂O₂
• 分子量: 232.282
• InChiKey: MIQMDNQMCFYTRD-UHFFFAOYSA-N

物化性质

• 沸点：
  501.4±50.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,3-dihydroxypropyl)-2-methyl-4-quinolinamine 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 3-bromo-N-(2,3-dihydroxypropyl)-2-methyl-4-quinolinamine
  参考文献：
  名称：

  Dihydro-1,4-oxazino(2,3-C)quinolines

  摘要：

  揭示了一种新型化合物，其化学式为##STR1## 其中X是氢、较低烷基、较低烷氧基、羟基、卤素、硝基或三氟甲基；R.sub.1是氢或较低烷基；R.sub.2是氢、较低烷基、芳基较低烷基或--(CH.sub.2).sub.m R.sub.7，其中m为1、2或3，R.sub.7是氰基或氨基；R.sub.3和R.sub.4独立地是氢或较低烷基；R.sub.5和R.sub.6独立地是氢或较低烷基，或R.sub.5 +R.sub.6与它们连接的碳原子一起构成环丁烷、环戊烷、环己烷、环庚烷、吡咯烷、哌啶、吗啉或硫代吗啉环，或者R.sub.5是氢，R.sub.6是芳基或--CH.sub.2 OR.sub.8，其中R.sub.8是氢、较低烷基或较低烷基羰基，这些化合物有助于增强记忆。

  公开号：

  US04743601A1
• 作为产物：
  描述：

  3-氨基-1,2-丙二醇 、 4-氯喹哪啶 以 水 为溶剂， 生成 N-(2,3-dihydroxypropyl)-2-methyl-4-quinolinamine
  参考文献：
  名称：

  Dihydro-1,4-oxazino(2,3-C)quinolines

  摘要：

  揭示了一种新型化合物，其化学式为##STR1## 其中X是氢、较低烷基、较低烷氧基、羟基、卤素、硝基或三氟甲基；R.sub.1是氢或较低烷基；R.sub.2是氢、较低烷基、芳基较低烷基或--(CH.sub.2).sub.m R.sub.7，其中m为1、2或3，R.sub.7是氰基或氨基；R.sub.3和R.sub.4独立地是氢或较低烷基；R.sub.5和R.sub.6独立地是氢或较低烷基，或R.sub.5 +R.sub.6与它们连接的碳原子一起构成环丁烷、环戊烷、环己烷、环庚烷、吡咯烷、哌啶、吗啉或硫代吗啉环，或者R.sub.5是氢，R.sub.6是芳基或--CH.sub.2 OR.sub.8，其中R.sub.8是氢、较低烷基或较低烷基羰基，这些化合物有助于增强记忆。

  公开号：

  US04743601A1

文献信息

• Dihydro-4(hydroxyalkyeneamino)quinolines
  申请人：Hoechst-Roussel Pharmaceuticals Incorporated

  公开号：US05182275A1

  公开（公告）日：1993-01-26

  There are disclosed novel compounds of the formula ##STR1## where X is hydrogen, loweralkyl, loweralkoxy, hydroxy, halogen, nitro or trifluoromethyl; R.sub.1 is hydrogen or loweralkyl; R.sub.2 is hydrogen, loweralkyl, arylloweralkyl or --(CH.sub.2).sub.m R.sub.7 wherein m is 1, 2 or 3 and R.sub.7 is cyano or amino; R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R.sub.5 and R.sub.6 are independently hydrogen or loweralkyl, or R.sub.5 +R.sub.6 taken together with the carbon atom to which they are attached constitute a cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyrrolidine, piperidine, morpholine or thiomorpholine ring, or R.sub.5 is hydrogen and R.sub.6 is aryl or --CH.sub.2 OR.sub.8 wherein R.sub.8 is hydrogen, loweralkyl or loweralkylcarbonyl, which are useful for enhancing memory.

  本发明公开了一种新型化合物的结构式，其中X为氢、低烷基、低烷氧基、羟基、卤素、硝基或三氟甲基；R1为氢或低烷基；R2为氢、低烷基、芳基低烷基或-(CH2)mR7，其中m为1、2或3，R7为氰基或氨基；R3和R4独立地为氢或低烷基；R5和R6独立地为氢或低烷基，或R5 + R6与它们附着的碳原子一起构成环丁烷、环戊烷、环己烷、环庚烷、吡咯烷、哌嗪烷、吗啉或硫代吗啉环，或R5为氢且R6为芳基或- OR8，其中R8为氢、低烷基或低烷基羰基，这些化合物对增强记忆有用。
• Hydroxyquinoline amines, and method of enhancing memory in mammals
  申请人：Hoechst-Roussel Pharmaceuticals Inc.

  公开号：US04942168A1

  公开（公告）日：1990-07-17

  There are disclosed novel compounds of the formula ##STR1## where X is hydrogen, loweralkyl, loweralkoxy, hydroxy, halogen, nitro or trifluoromethyl; R.sub.1 is hydrogen or loweralkyl; R.sub.2 is hydrogen, loweralkyl, arylloweralkyl or --(CH.sub.2).sub.m R.sub.7 wherein m is 1, 2 or 3 and R.sub.7 is cyano or amino; R.sub.3 and R.sub.4 are independently hydrogen or loweralkyl; R.sub.5 and R.sub.6 are independently hydrogen or loweralkyl, or R.sub.5 +R.sub.6 taken together with the carbon atom to which they are attached constitute a cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyrrolidine, piperidine, morpholine or thiomorpholine ring, or R.sub.5 is hydrogen and R.sub.6 is aryl or --CH.sub.2 OR.sub.8 wherein R.sub.8 is hydrogen, loweralkyl or loweralkylcarbonyl, which are useful for enhancing memory.

  本发明公开了一种新型化合物，其化学式为##STR1##其中X为氢、低碳基、低氧基、羟基、卤素、硝基或三氟甲基；R.sub.1为氢或低碳基；R.sub.2为氢、低碳基、芳基低碳基或--(CH.sub.2).sub.m R.sub.7，其中m为1、2或3，R.sub.7为氰基或氨基；R.sub.3和R.sub.4分别为氢或低碳基；R.sub.5和R.sub.6分别为氢或低碳基，或R.sub.5+R.sub.6与它们附着的碳原子一起构成环丁烷、环戊烷、环己烷、环庚烷、吡咯烷、哌嗪烷、吗啉或硫代吗啉环，或R.sub.5为氢，R.sub.6为芳基或--CH.sub.2 OR.sub.8，其中R.sub.8为氢、低碳基或低碳基酰基，其对增强记忆有用。
• Dihydro-1,4-oxazino(2,3-c)quinolines, a process and intermediates for the preparation thereof and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0299345A2

  公开（公告）日：1989-01-18

  The present application relates to compounds of the formula I where X is hydrogen, loweralkyl, loweralkoxy, hydroxy, halogen, nitro or trifluoromethyl; R₁ is hydrogen or loweralkyl; R₂ is hydrogen, loweralkyl, arylloweralkyl or -(CH₂)mR₇ wherein m is 1, 2 or 3 and R₇ is cyano or amino; R₃ and R₄ are independently hydrogen or loweralkyl; R₅ and R₆ are independently hydrogen or loweralkyl, or R₅+R₆ taken together with the carbon atom to which they are attached constitute a cyclobutane, cyclopentane, cyclohexane, cycloheptane, pyrrolidine, piperidine, morpholine or thiomorpholine ring, or R₅ is hydrogen and R₆ is aryl or -CH₂OR₈ wherein R₈ is hydrogen, loweralkyl or loweralkylcarbonyl, which are useful for enhancing memory. and a process for their preparation. The invention relates also to compounds of the formula II where X, R₁ and R₃ through R₆ are as defined earlier and R₉ is hydrogen or bromine (with the proviso that when R₁=R₃=R₄=R₅=R₆=R₉=H, X is not 7-chloro) which are also useful for enhancing memory and for preparing compounds of formula I.

  本申请涉及式 I 的化合物 其中 X 是氢、低级烷基、低级烷氧基、羟基、卤素、硝基或三氟甲基；R₁ 是氢或低级烷基；R₂ 是氢、低级烷基、芳基低级烷基或-(CH₂)mR₇，其中 m 是 1、2 或 3，R₇ 是氰基或氨基；R₃ 和 R₄ 独立地是氢或低级烷基；R₅ 和 R₆ 独立地为氢或低级烷基，或 R₅+R₆ 与它们所连接的碳原子一起构成环丁烷、环戊烷、环己烷、环庚烷吡咯烷、哌啶、吗啉或硫代吗啉环，或 R₅ 为氢且 R₆ 为芳基或 -CH₂OR₈ 其中 R₈ 为氢、低级烷基或低级烷基羰基。及其制备工艺。 本发明还涉及式 II 的化合物 其中 X、R₁ 和 R₃ 至 R₆ 如前定义，R₉ 是氢或溴 (但当 R₁=R₃=R₄=R₅=R₆=R₉=H 时，X 不是 7-氯)，这些化合物也有助于增强记忆力和制备式 I 的化合物。
• 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.
• US4743601A
  申请人：——

  公开号：US4743601A

  公开（公告）日：1988-05-10