3-amino-4-(methylamino)quinoline | 99010-10-3

• 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-(methylamino)quinoline
• 英文别名: 4-N-methylquinoline-3,4-diamine
• CAS: 99010-10-3
• 化学式: C₁₀H₁₁N₃
• 分子量: 173.217
• InChiKey: OGAYBYZECXWINC-UHFFFAOYSA-N

物化性质

• 沸点：
  354.2±32.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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-(methylamino)quinoline 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-methyl-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-(methylamino)-3-nitroquinoline 在 钯 氢气 、 silica gel 、 chloroform methanol 作用下， 以 乙醇 为溶剂， 以affords 600 mg (41%) of 3-amino-4-methylaminoquinoline的产率得到3-amino-4-(methylamino)quinoline
  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

• 1H-imidazo[4,5-c]quinolines and their use as bronchodilating agents
  申请人：Riker Laboratories, Inc.

  公开号：US04698348A1

  公开（公告）日：1987-10-06

  1H-imidazo[4,5-c]quinoline which are bronchodilators. Pharmacological methods of using the compounds as bronchodilators, pharmaceutical compositions containing the compounds, and synthetic intermediate for preparing the compounds are also described.

  1H-咪唑并[4,5-c]喹啉是支气管扩张剂。描述了使用这些化合物作为支气管扩张剂的药理学方法，含有这些化合物的药物组合物，以及用于制备这些化合物的合成中间体。
• 1H-Imidazo[4,5-c]quinolin-4-amines and antiviral use
  申请人：Riker Laboratories, Inc.

  公开号：US04689338A1

  公开（公告）日：1987-08-25

  1H-Imidazo[4,5-c]quinolin-4-amines which are antivirals. Pharmacological methods of using such compounds and pharmaceutical compositions containing such compounds are also described.

  1H-咪唑并[4,5-c]喹啉-4-胺是抗病毒药物。还描述了使用这些化合物的药理学方法以及含有这些化合物的药物组合物。
• Imidazoquinolone derivatives
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US04994468A1

  公开（公告）日：1991-02-19

  Novel imidazoquinolone derivative represented by the formula (I); ##STR1## wherein R.sup.1 represents hydrogen, alkyl, cycloalkyl, alkenyl aralkyl, aralkenyl or substituted or unsubstituted aryl; X represents nitrogen or ##STR2## where R.sup.2 is hydrogen, hydroxyl, alkyl, cycloalkyl, alkenyl, aralkyl, aralkenyl, substituted or unsubstituted aryl, thiol, halogen, substituted or unsubstituted aromatic heterocyclic group, or --(CH.sub.2).sub.m CO.sub.2 R.sup.6 where R.sup.6 is hydrogen or lower alkyl and m is an integer of 0 to 3; Y represents oxygen or sulfur; R.sup.3 represents alkyl, cycloalkyl, alkoxyalkly, alkenyl, aralkyl, aralkenyl, --(CH.sub.2).sub.n -- Het where Het is substituted or unsubstituted aromatic heterocyclic group and n is an integer of 1 to 3 or --(CH.sub.2).sub.n CO.sub.2 R.sup.6a where n has the same meaning as defined above and R.sup.6a has the same meaning as defined as to R.sup.6 ; each of R.sup.4 and R.sup.5 independently represents hydrogen, lower alkyl, trifluoromethyl, cycloalkyl, halogen, hydroxyl, lower alkoxyl, lower alkylthio, nitro, amino, lower alkylamino, lower alkanoylamino, aroylamino, lower alkanoyl or aroyl; and a pharmaceutically acceptable salt thereof. The Compound (I) and a pharmaceutically acceptable salt thereof show bronchodilatory and antiallergic activities, and are useful for treating respiratory disorders such as bronchial asthma.

  新型咪唑喹酮衍生物的化学式（I）所代表的是：其中R.sup.1代表氢、烷基、环烷基、烯基芳基、烯基芳基或取代或未取代芳基；X代表氮或##STR2##其中R.sup.2为氢、羟基、烷基、环烷基、烯基、芳基、硫醇、卤素、取代或未取代芳香杂环基，或--（CH.sub.2）.sub.m CO.sub.2 R.sup.6，其中R.sup.6为氢或较低烷基，m为0到3的整数；Y代表氧或硫；R.sup.3代表烷基、环烷基、烷氧基烷基、烯基、芳基、烯基芳基、--（CH.sub.2）.sub.n -- Het，其中Het为取代或未取代芳香杂环基，n为1到3的整数，或--（CH.sub.2）.sub.n CO.sub.2 R.sup.6a，其中n具有上述定义的相同含义，R.sup.6a具有与R.sup.6相同的定义；R.sup.4和R.sup.5中的每一个独立地代表氢、较低烷基、三氟甲基、环烷基、卤素、羟基、较低烷氧基、较低烷基硫基、硝基、氨基、较低烷基氨基、较低烷酰胺基、芳酰胺基、较低烷酰基或芳酰基；以及其药学上可接受的盐。化合物（I）及其药学上可接受的盐具有支气管扩张和抗过敏活性，并且可用于治疗支气管哮喘等呼吸系统疾病。
• 2-substituted carbonylimidazo[4,5-c]quinolines
  申请人：Shionogi & Co., Ltd.

  公开号：US04940714A1

  公开（公告）日：1990-07-10

  2-Substituted carbonylimidazo[4,5-c]quinolines of formula: ##STR1## having a high affinity for benzodiazepin receptor and showing an excellent psychostimulating action orally at a dose of 0.1-500 mg are provided through several routes.

  提供了几种途径合成具有高亲和力的苯二氮平受体和在口服剂量为0.1-500毫克时显示出优异的精神刺激作用的式为##STR1##的2-取代羰基咪唑[4,5-c]喹啉。
• 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。