(5R)-N-甲基-5,6-二氢-4H-咪唑并[4,5,1-Ij]喹啉-5-胺 | 185943-30-0

• 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
• 中文名称: (5R)-N-甲基-5,6-二氢-4H-咪唑并[4,5,1-Ij]喹啉-5-胺
• 中文别名: 4H-咪唑并[4,5,1-ij]喹啉-5-胺,5,6-二氢-N-甲基-,(R)-(9CI)
• 英文名称: (10R)-N-Methyl-1,3-diazatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-10-amine
• CAS: 185943-30-0
• 化学式: C₁₁H₁₃N₃
• 分子量: 187.244
• InChiKey: BGMDLAIZBKXVQQ-SECBINFHSA-N

物化性质

• 沸点：
  373.9±52.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (5R)-N-甲基-5,6-二氢-4H-咪唑并[4,5,1-Ij]喹啉-5-胺 在 甲酸 作用下， 反应 1.0h， 生成 (R)-5,6-Dihydro-4H-imidazo[4,5,1-ij]quinolin-5-yl-dimethyl-amine
  参考文献：
  名称：

  Synthesis and Biological Activities of (R)-5,6-Dihydro-N,N-dimethyl-4H-imidazo[4,5,1-ij]quinolin-5-amine and Its Metabolites

  摘要：

  The imidazoquinoline (R)-5,6-dihydro-N,N-dimethyl-4H-imidazo[(R)-3] is a potent dopamine agonist when tested in animals but surprisingly shows very low affinity in in vitro binding assays. When incubated with mouse or monkey liver S9 microsomes, (R)-3 is metabolized by N-demethylation and oxidation to (R)-5,6-dihydro-5-(methylamino)-4H-imidazo[4,5,1-ij]quinolin-2(lu)-one [(R)-6]; intermediate metabolites, where N-demethylation to the imidazoquinoline (R)-4 and where oxidation to the imidazoquinolinone (R)-5 has taken place, are also observed in these incubates. A cross-species study on the metabolism of (R)-3 in vitro has shown large variations in the extent of metabolism from species to species. Imidazoquinolinones (R)-5 and (R)-6 have comparable activity to (R)-3 in animals and also show good dopaminergic (D2) and serotonergic (5HT(1A)) activities in binding assays. It is probable that these metabolites account at least in part for the in vivo activity found for (R)-3. Efficient syntheses for compounds 3-6 as single enantiomers from quinoline are presented together with information on the biological activities and metabolic stabilities of these compounds.

  DOI：

  10.1021/jm960360q
• 作为产物：
  描述：

  (10R)-N-benzyl-N-methyl-1,3-diazatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-10-amine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 55.0 ℃ 、344.73 kPa 条件下， 反应 18.0h， 生成 (5R)-N-甲基-5,6-二氢-4H-咪唑并[4,5,1-Ij]喹啉-5-胺
  参考文献：
  名称：

  Synthesis and Biological Activities of (R)-5,6-Dihydro-N,N-dimethyl-4H-imidazo[4,5,1-ij]quinolin-5-amine and Its Metabolites

  摘要：

  The imidazoquinoline (R)-5,6-dihydro-N,N-dimethyl-4H-imidazo[(R)-3] is a potent dopamine agonist when tested in animals but surprisingly shows very low affinity in in vitro binding assays. When incubated with mouse or monkey liver S9 microsomes, (R)-3 is metabolized by N-demethylation and oxidation to (R)-5,6-dihydro-5-(methylamino)-4H-imidazo[4,5,1-ij]quinolin-2(lu)-one [(R)-6]; intermediate metabolites, where N-demethylation to the imidazoquinoline (R)-4 and where oxidation to the imidazoquinolinone (R)-5 has taken place, are also observed in these incubates. A cross-species study on the metabolism of (R)-3 in vitro has shown large variations in the extent of metabolism from species to species. Imidazoquinolinones (R)-5 and (R)-6 have comparable activity to (R)-3 in animals and also show good dopaminergic (D2) and serotonergic (5HT(1A)) activities in binding assays. It is probable that these metabolites account at least in part for the in vivo activity found for (R)-3. Efficient syntheses for compounds 3-6 as single enantiomers from quinoline are presented together with information on the biological activities and metabolic stabilities of these compounds.

  DOI：

  10.1021/jm960360q

文献信息

• Heterocyclic amines having central nervous system activity
  申请人：Romero Glenn Arthur

  公开号：US20050107378A1

  公开（公告）日：2005-05-19

  Tricyclic nitrogen containing compounds, having anxiolytic and anti-depressant activity and central nervous system activity of the following structural formula and pharmaceutically acceptable salts thereof wherein R 1 and R 2 are independently hydrogen, C 1-6 alkyl or R 1 and R 2 are joined to form pyrrolidine, piperidine, morpholine or imidazole. X is OCH 3 , SO 2 R 3 , SO 2 CF 3 or CN where R 3 is C 1-6 alkyl or an Aryl; and Y is hydrogen, Cl, Br, F, CN, CONR 1 R 2 , CF 3 , OCH 3 , SO 2 NR 1 R 2 . These new compounds are suitable for treating anxiolytic disorder, schizophrenia, Parkinson's disease, anxiety, depression or as compounds for lowering blood pressure or treating migraine headaches in patients in need of such treatment.

  具有抗焦虑和抗抑郁活性以及中枢神经系统活性的三环氮含有化合物，其结构式如下，并且其药学上可接受的盐，其中R1和R2独立地为氢，C1-6烷基或R1和R2结合形成吡咯烷，哌嗪，吗啉或咪唑。X为OCH3，SO2R3，SO2CF3或CN，其中R3为C1-6烷基或芳基；而Y为氢，Cl，Br，F，CN，CONR1R2，CF3，OCH3，SO2NR1R2。这些新化合物适用于治疗焦虑症，精神分裂症，帕金森病，焦虑，抑郁症或作为降低血压或治疗需要此类治疗的偏头痛患者的化合物。
• [EN] USE OF GROWTH HORMONE SECRETAGOGUES FOR TREATMENT OF FIBROMYALGIA<br/>[FR] UTILISATION DE SÉCRÉTAGOGUES DE L'HORMONE DE CROISSANCE POUR LE TRAITEMENT DE LA FIBROMYALGIE
  申请人：PFIZER PROD INC

  公开号：WO2004108120A1

  公开（公告）日：2004-12-16

  This invention is directed to a method of treating fibromyalgia in a patient which comprises administering a growth hormone secretagogue, prodrugs thereof or pharmaceutically acceptable salts of said secretagogues or said prodrugs to a patient in need thereof. The present invention provides such a method wherein the growth hormone secretagogue is a compound of Formula I: a prodrug thereof or a pharmaceutically acceptable salt of said secretagogue or said prodrug and wherein the variables HET, R3, R4, X4, R6, R7 and R8 are as defined in the specification.
• Synthesis and Biological Activities of (<i>R</i>)-5,6-Dihydro-<i>N</i>,<i>N</i>-dimethyl-4<i>H</i>-imidazo[4,5,1-<i>ij</i>]quinolin-5-amine and Its Metabolites
  作者：Richard F. Heier、Lester A. Dolak、J. Neil Duncan、Deborah K. Hyslop、Michael F. Lipton、Iain J. Martin、Michael A. Mauragis、Montford F. Piercey、Nanette F. Nichols、Peggy J. K. D. Schreur、Martin W. Smith、Malcolm W. Moon

  DOI：10.1021/jm960360q

  日期：1997.2.1

  The imidazoquinoline (R)-5,6-dihydro-N,N-dimethyl-4H-imidazo[(R)-3] is a potent dopamine agonist when tested in animals but surprisingly shows very low affinity in in vitro binding assays. When incubated with mouse or monkey liver S9 microsomes, (R)-3 is metabolized by N-demethylation and oxidation to (R)-5,6-dihydro-5-(methylamino)-4H-imidazo[4,5,1-ij]quinolin-2(lu)-one [(R)-6]; intermediate metabolites, where N-demethylation to the imidazoquinoline (R)-4 and where oxidation to the imidazoquinolinone (R)-5 has taken place, are also observed in these incubates. A cross-species study on the metabolism of (R)-3 in vitro has shown large variations in the extent of metabolism from species to species. Imidazoquinolinones (R)-5 and (R)-6 have comparable activity to (R)-3 in animals and also show good dopaminergic (D2) and serotonergic (5HT(1A)) activities in binding assays. It is probable that these metabolites account at least in part for the in vivo activity found for (R)-3. Efficient syntheses for compounds 3-6 as single enantiomers from quinoline are presented together with information on the biological activities and metabolic stabilities of these compounds.