tert-butyl (8-amino-1,2,3,4-tetrahydro-3-quinolinyl)carbamate | 132874-65-8

• 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: tert-butyl (8-amino-1,2,3,4-tetrahydro-3-quinolinyl)carbamate
• 英文别名: t-butyl (8-amino-1,2,3,4-tetrahydro-3-quinolyl)carbamate；tert-butyl N-(8-amino-1,2,3,4-tetrahydroquinolin-3-yl)carbamate
• CAS: 132874-65-8
• 化学式: C₁₄H₂₁N₃O₂
• 分子量: 263.34
• InChiKey: ORYBTYQIBBFCRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (8-amino-1,2,3,4-tetrahydro-3-quinolinyl)carbamate 在 盐酸 、 sodium methylate 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 10.08h， 生成 5-(propylamino)-5,6-dihydro-4H-imidazo<4,5,1-ij>quinolin-2(1H)-one
  参考文献：
  名称：

  Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds

  摘要：

  The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (5), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of 5; the (S)-enantiomer shows no dopaminergic activity. A series of analogues where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared. Some of these compounds showed a combination of dopaminergic and serotonergic activity, while one compound, 6-(dipropylamino)-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinazolin-3-one (24), was a selective serotonergic agonist. Various analogues of 5 where the dipropylamine substituent was modified were prepared. Most of these showed reduced dopaminergic activity, while several were as potent as 5 at the serotonin 5HT1A receptor. Orientations for the new compounds at dopamine and serotonin receptors are proposed and compared with those of other tricyclic ligands known to have high affinity at these receptors.

  DOI：

  10.1021/jm00084a013
• 作为产物：
  描述：

  6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinamine 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 19.0h， 生成 tert-butyl (8-amino-1,2,3,4-tetrahydro-3-quinolinyl)carbamate
  参考文献：
  名称：

  Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds

  摘要：

  The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (5), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of 5; the (S)-enantiomer shows no dopaminergic activity. A series of analogues where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared. Some of these compounds showed a combination of dopaminergic and serotonergic activity, while one compound, 6-(dipropylamino)-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinazolin-3-one (24), was a selective serotonergic agonist. Various analogues of 5 where the dipropylamine substituent was modified were prepared. Most of these showed reduced dopaminergic activity, while several were as potent as 5 at the serotonin 5HT1A receptor. Orientations for the new compounds at dopamine and serotonin receptors are proposed and compared with those of other tricyclic ligands known to have high affinity at these receptors.

  DOI：

  10.1021/jm00084a013
• 作为试剂：
  描述：

  tert-butyl (6-bromo-1,2,3,4-tetrahydro-8-nitro-3-quinolinyl)carbamate 、 氢气 在 钯 乙酸乙酯 、 sodium hydroxide 、 tert-butyl (8-amino-1,2,3,4-tetrahydro-3-quinolinyl)carbamate 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以to give 2.72 g of t-butyl (8-amino-1,2,3,4-tetrahydro-3-quinolyl)carbamate (compound XXXII) as an oil的产率得到tert-butyl (8-amino-1,2,3,4-tetrahydro-3-quinolinyl)carbamate
  参考文献：
  名称：

  Heterocyclic amines having central nervous system activity

  摘要：

  含有三环氮化合物，具有以下结构式的中枢神经系统活性：##STR1##和其药学上可接受的盐，其中R.sub.1，R.sub.2和R.sub.3独立地是氢，C.sub.1-6烷基，烯基或炔基，C.sub.3-10环烷基，或R.sub.1和R.sub.2连接形成可以包含额外杂原子的C.sub.3-7环胺；X是氢，C.sub.1-6烷基，卤素，羟基，烷氧基，氰基，羧酰胺，羧基或羧基烷氧基；A是SO.sub.2，N，CH，CH.sub.2，CHCH.sub.3，C=O，C=S，C-SCH.sub.3，C=NH，C-NH.sub.2，C-NHCH.sub.3，CNHCOOCH.sub.3或C-NHCN。B是CH.sub.2，CH，C=O，N，NH或N-CH.sub.3；n为0或1；D是CH，CH.sub.2，C=O，0，N，NH或N-CH.sub.3。这些新化合物适用于治疗精神分裂症、帕金森病、焦虑症、抑郁症或作为降低动物或人体内血压的化合物。

  公开号：

  US05436240A1

文献信息

• Heterocyclic amines having central nervous system activity
  申请人：The Upjohn Company

  公开号：US05273975A1

  公开（公告）日：1993-12-28

  Tricyclic nitrogen containing compounds, having central nervous system activity of the following structural formula: ##STR1## and pharmaceutically acceptable salts thereof wherein R.sub.1, R.sub.2, and R.sub.3 are independently hydrogen, C.sub.1-6 alkyl, alkenyl, or alkynyl, C.sub.3-10 cycloalkyl, or R.sub.1 and R.sub.2 are joined to form a C.sub.3-7 cyclic amine which can contain additional heteroatoms; X is hydrogen, C.sub.1-6 alkyl halogen, hydroxy, alkoxy, cyano, carboxamide, carboxyl, or carboalkoxyl; A is SO.sub.2, N, CH, CH.sub.2, CHCH.sub.3, C.dbd.O, C.dbd.S, C-SCH.sub.3, C.dbd.NH, C-NH.sub.2, C-NHCH.sub.3, C--NHCOOCH.sub.3, or C--NHCN. B is CH.sub.2, CH, C.dbd.O, N, NH or N--CH.sub.3 ; n is 0 or 1; and D is CH, CH.sub.2, C.dbd.O, O, N, NH or N--CH.sub.3. These new compounds are suitable for treating schizophrenia, Parkinson's disease, anxiety, depression or as compounds for lowering blood pressure in animal or human hosts.

  三环氮含化合物，具有以下结构式的中枢神经系统活性：##STR1##及其药学上可接受的盐，其中R.sub.1、R.sub.2和R.sub.3独立地是氢、C.sub.1-6烷基、烯基或炔基、C.sub.3-10环烷基，或R.sub.1和R.sub.2连接形成可含有额外杂原子的C.sub.3-7环胺；X是氢、C.sub.1-6烷基卤素、羟基、烷氧基、氰基、羧酰胺、羧基或羧烷氧基；A是SO.sub.2、N、CH、CH.sub.2、CHCH.sub.3、C.dbd.O、C.dbd.S、C-SCH.sub.3、C.dbd.NH、C-NH.sub.2、C-NHCH.sub.3、C--NHCOOCH.sub.3或C--NHCN。B是CH.sub.2、CH、C.dbd.O、N、NH或N--CH.sub.3；n为0或1；D是CH、CH.sub.2、C.dbd.O、O、N、NH或N--CH.sub.3。这些新化合物适用于治疗精神分裂症、帕金森病、焦虑、抑郁或作为降低动物或人类宿主血压的化合物。
• Dopaminergic and serotonergic activities of imidazoquinolinones and related compounds
  作者：Malcolm W. Moon、Jeanette K. Morris、Richard F. Heier、Connie G. Chidester、William E. Hoffmann、Montford F. Piercey、John S. Althaus、Philip F. VonVoigtlander、Dawna L. Evans

  DOI：10.1021/jm00084a013

  日期：1992.3

  The synthesis of 5-(dipropylamino)-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (5), a potent dopamine D2 agonist showing high dopamine/serotonin (5HT1A) selectivity, is described. Dopaminergic activity is associated with the (R)-enantiomer of 5; the (S)-enantiomer shows no dopaminergic activity. A series of analogues where the imidazolone ring was modified to various 5- or 6-membered heterocyclic rings were prepared. Some of these compounds showed a combination of dopaminergic and serotonergic activity, while one compound, 6-(dipropylamino)-1,2,6,7-tetrahydro-3H,5H-pyrido[3,2,1-ij]quinazolin-3-one (24), was a selective serotonergic agonist. Various analogues of 5 where the dipropylamine substituent was modified were prepared. Most of these showed reduced dopaminergic activity, while several were as potent as 5 at the serotonin 5HT1A receptor. Orientations for the new compounds at dopamine and serotonin receptors are proposed and compared with those of other tricyclic ligands known to have high affinity at these receptors.