3-amino-4-ethylaminoquinoline | 99010-13-6

• 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: 3-amino-4-ethylaminoquinoline
• 英文别名: 4-N-ethylquinoline-3,4-diamine
• CAS: 99010-13-6
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: NECFGUMXYZTAKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-4-ethylaminoquinoline 在 过氧乙酸 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-Chloro-1-ethyl-1H-imidazo[4,5-c]quinoline
  参考文献：
  名称：

  Synthesis and Structure−Activity-Relationships of 1H-Imidazo[4,5-c]quinolines That Induce Interferon Production

  摘要：

  1H-Imidazo-[4,5-c]quinolines were prepared while investigating novel nucleoside analogues as potential antiviral agents. While these compounds showed no direct antiviral activity when tested in a number of cell culture systems, some demonstrated potent inhibition of virus lesion development in an intravaginal guinea pig herpes simplex virus-2 assay. We have determined that the in vivo antiviral activity can be attributed to the ability of these molecules to induce the production of cytokines, especially interferon (IFN), in this model. Subsequently, we found that the compounds also induce in vitro production of IFN in human peripheral blood mononuclear cells (hPBMCs). The in vitro results reported herein and the in vivo results reported previously led to the discovery of imiquimod, 26, which was developed as a topical agent and has been approved for the treatment of genital warts, actinic keratosis, and superficial basal cell carcinoma.

  DOI：

  10.1021/jm049211v
• 作为产物：
  描述：

  4-ethylamino-3-nitroquinoline 在 钯 作用下， 以 乙醇 为溶剂， 以to give 0.95 g (82%) of 3-amino-4-ethylaminoquinoline的产率得到3-amino-4-ethylaminoquinoline
  参考文献：
  名称：

  Condensed imidazopyridine derivatives useful as psychotropic agents

  摘要：

  提供了一种公式为：## STR1 ##的化合物（其中R是苯基，可以选择从三氟甲基，C.sub.1-C.sub.5烷基，C.sub.1-C.sub.5烷氧基，C.sub.1-C.sub.5烷硫基，硝基，氨基C.sub.1-C.sub.5烷酰胺基和C.sub.1-C.sub.5烷氧羰基或选择从卤素，C.sub.1-C.sub.5烷基和C.sub.1-C.sub.5烷氧基的群中选择一个或两个成员，Q是氢，C.sub.1-C.sub.5烷基，C.sub.1-C.sub.10酰基，C.sub.1-C.sub.5烷基磺酰基或C.sub.6-C.sub.10芳基磺酰基，##STR2## R.sup.1，R.sup.2，R.sup.3和R.sup.4分别为氢，卤素C.sub.1-C.sub.5烷基，C.sub.1-C.sub.5烷氧基或C.sub.1-C.sub.5卤代烷基，Q存在于1,3或5位的氮原子上，虚线表示在2,3；3a,3b；4,5 / 1,3b；2,3；3a,4 /或1,2；3a,3b；4,5的位置存在三个双键）或其盐，可用作精神刺激剂或抗焦虑剂。

  公开号：

  US04753951A1

文献信息

• Novel Compounds
  申请人：Isobe Yoshiaki

  公开号：US20110136801A1

  公开（公告）日：2011-06-09

  The present invention provides compounds of formula (I): wherein R a , R b , R c , R 1 , R 2 , R 3 , X 1 , Y 1 , Z 1 , A, n and m are as defined in the specification, and pharmaceutically acceptable salts thereof, as well as processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了如下式（I）的化合物： 其中R a ，R b ，R c ，R 1 ，R 2 ，R 3 ，X 1 ，Y 1 ，Z 1 ，A，n和m如规范中所定义， 以及其药学上可接受的盐，以及它们的制备方法，含有它们的药物组合物以及它们在治疗中的应用。
• Condensed imidazopyridine derivatives useful as psychotropic agents
  申请人：Shionogi & Co., Ltd.

  公开号：US04753951A1

  公开（公告）日：1988-06-28

  A compound of the formula: ##STR1## (wherein R is phenyl optionally substituted by one or two members selected from the group consisting of trifluoromethyl, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkylthio, nitro, amino C.sub.1 -C.sub.5 alkanoylamino and C.sub.1 -C.sub.5 alkoxycarbonyl or 5- or 6-membered heterocyclic group optionally substituted by one or two members selected from the group consisting of halogen, C.sub.1 -C.sub.5 alkyl and C.sub.1 -C.sub.5 alkoxy, Q is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.10 acyl, C.sub.1 -C.sub.5 alkylsulfonyl or C.sub.6 -C.sub.10 arylsulfonyl, ##STR2## R.sup.1, R.sup.2, R.sup.3, and R.sup.4 each is hydrogen, halogen C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy or C.sub.1 -C.sub.5 haloalkyl, Q is present on the nitrogen atom of the 1,3 or 5-position, and the dotted line indicates the presence of three double bonds at the position of 2, 3; 3a, 3b; 4, 5 / 1, 3b; 2, 3; 3a, 4 / or 1, 2; 3a, 3b; 4, 5) or its salt, being useful as psychostimulants or anxiolytics, is provided.

  提供了一种公式为：## STR1 ##的化合物（其中R是苯基，可以选择从三氟甲基，C.sub.1-C.sub.5烷基，C.sub.1-C.sub.5烷氧基，C.sub.1-C.sub.5烷硫基，硝基，氨基C.sub.1-C.sub.5烷酰胺基和C.sub.1-C.sub.5烷氧羰基或选择从卤素，C.sub.1-C.sub.5烷基和C.sub.1-C.sub.5烷氧基的群中选择一个或两个成员，Q是氢，C.sub.1-C.sub.5烷基，C.sub.1-C.sub.10酰基，C.sub.1-C.sub.5烷基磺酰基或C.sub.6-C.sub.10芳基磺酰基，##STR2## R.sup.1，R.sup.2，R.sup.3和R.sup.4分别为氢，卤素C.sub.1-C.sub.5烷基，C.sub.1-C.sub.5烷氧基或C.sub.1-C.sub.5卤代烷基，Q存在于1,3或5位的氮原子上，虚线表示在2,3；3a,3b；4,5 / 1,3b；2,3；3a,4 /或1,2；3a,3b；4,5的位置存在三个双键）或其盐，可用作精神刺激剂或抗焦虑剂。
• Substituted Imidazo Ring Systems and Methods
  申请人：Dellaria F. Joseph

  公开号：US20070259881A1

  公开（公告）日：2007-11-08

  Imidazo ring systems, which include, for example, imidazopyridine, imidazoquinoline, 6,7,8,9-tetrahydroimidazoquinoline, imidazonaphthyridine, and 6,7,8,9-tetrahydroimidazonaphthyridine compounds substituted at the 1-position and/or the 2-position, pharmaceutical compositions containing these compounds, methods of making these compounds, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本文介绍了咪唑环系统，包括咪唑吡啶、咪唑喹啉、6,7,8,9-四氢咪唑喹啉、咪唑萘啶和6,7,8,9-四氢咪唑萘啶化合物，这些化合物在1位和/或2位被取代，以及含有这些化合物的药物组合物，制备这些化合物的方法，以及将这些化合物用作免疫调节剂的方法，用于在动物中诱导细胞因子生物合成和治疗包括病毒性和肿瘤性疾病的方法。
• IMIDAZOQUINOLINES WITH IMMUNO-MODULATING PROPERTIES
  申请人：Bonnert Roger Victor

  公开号：US20100280001A1

  公开（公告）日：2010-11-04

  The present invention provides compounds of formula (I) wherein R a , R 1 , R 2 , R 3 , X 1 , Y 1 , Z 1 , A, n and m are as defined in the specification, and pharmaceutically acceptable salts thereof, as well as processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了式(I)的化合物，其中Ra、R1、R2、R3、X1、Y1、Z1、A、n和m如规范中定义，以及其药学上可接受的盐，以及它们的制备方法、含有它们的制药组合物和它们在治疗中的应用。
• Imidazoquinolines with Immuno-Modulating Properties
  申请人：AstraZeneca AB

  公开号：US20130225555A1

  公开（公告）日：2013-08-29

  The present invention provides compounds of formula (I) wherein R a , R 1 , R 2 , R 3 , X 1 , Y 1 , Z 1 , A, n and m are as defined in the specification, and pharmaceutically acceptable salts thereof, as well as processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

  本发明提供了式（I）的化合物，其中Ra，R1，R2，R3，X1，Y1，Z1，A，n和m如规范中所定义，并且其药学上可接受的盐，以及它们的制备方法，含有它们的制药组合物和它们在治疗中的应用。