(+/-)-1-propionyl-3-dimethylamino-6,7-dimethoxy-1,2,3,4-tetrahydroquinoline

• 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: (+/-)-1-propionyl-3-dimethylamino-6,7-dimethoxy-1,2,3,4-tetrahydroquinoline
• 英文别名: 1-propionyl-3-dimethylamino-6,7-dimethoxy-1,2,3,4-tetrahydroquinoline；1-[3-(dimethylamino)-6,7-dimethoxy-3,4-dihydro-2H-quinolin-1-yl]propan-1-one
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: AELKMGQKMDEPIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  42
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-dimethylamino-6,7-dimethoxyquinoline 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 25.0~80.0 ℃ 、399.99 kPa 条件下， 反应 4.0h， 生成 (+/-)-1-propionyl-3-dimethylamino-6,7-dimethoxy-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Synthesis and positive inotropic effect of 1-alkyl- and 1-acyl-6,7-dimethoxy-3-dimethylamino-1,2,3,4-tetrahydroquinolines

  摘要：

  In the search for new positive inotropic agents we have investigated a series of 3-dimethylamino-1,2,3,4-tetrahydroquinolines with various substituents on the nitrogen of the quinoline ring. The N-isobutyryl derivative 20 (S903) was selected as the most interesting compound. Interestingly, while cardiac contractility was increased in vitro, heart rate was unchanged or slightly decreased. The positive inotropic activity was partly dependent on an indirect sympathomimetic effect. The (S) absolute configuration of the (-)enantiomer of S903 was established by correlation with (S)-L-dopa.

  DOI：

  10.1016/0223-5234(94)90110-4

文献信息

• Process for Synthesis of Chiral 3-Substituted Tetrahydroquinoline Derivatives
  申请人：Council of Scientific & Industrial Research

  公开号：US20150038714A1

  公开（公告）日：2015-02-05

  The present invention relates to novel and concise process for the construction of chiral 3-substituted tetrahyroquinoline derivatives based on proline catalyzed asymmetric α-functionalization of aldehyde, followed by in situ reductive cyclization of nitro group under catalytic hydrogenation condition with high optical purities. Further the invention relates to conversion of derived chiral 3-substituted tetrahydroquinoline derivatives into therapeutic agents namely (−)-sumanirole (96% ee) and 1-[(S)-3-(di-methylamino)-3,4-dihydro-6,7-dimethoxy-quinolin-1(2H)-yl]propanone[(S)-903] (92% ee).

  该发明涉及一种新颖简洁的过程，用于构建基于脯氨酸催化的醛的手性3-取代四氢喹啉衍生物的立体选择性α-官能化，随后在高光学纯度的催化氢化条件下通过硝基基团的原位还原环化。此外，该发明涉及将衍生的手性3-取代四氢喹啉衍生物转化为治疗剂，即(−)-sumanirole（96% ee）和1-[(S)-3-(二甲氨基)-3,4-二產二甲氧基喹啉-1(2H)-基]丙酮[(S)-903]（92% ee）。
• N1-acyl-3-amino-1,2,3,4-tetrahydroquinoline compounds
  申请人：SIMES S.p.A. Società Italiana Medicinali e Sintetici

  公开号：EP0072070A2

  公开（公告）日：1983-02-16

  N,-acyl-3-amino-1,2,3,4-tetrahydroquinoline compounds acting on the cardiocirculatory system, pharmaceutically acceptable salts thereof, pharmaceutical compositions containing the new compounds and some intermediates useful in the preparation of the new tetrahydroquinoline compounds. Process for preparing the new tetrahydroquinoline compounds and some intermediates useful in the preparation thereof.

  N,-酰基-3-氨基-1,2,3,4-四氢喹啉化合物、其药学上可接受的盐、含有新化合物的药物组合物以及一些用于制备新四氢喹啉化合物的中间体。 制备新四氢喹啉化合物及其制备过程中有用的一些中间体的工艺。
• US4507307A
  申请人：——

  公开号：US4507307A

  公开（公告）日：1985-03-26
• US9163038B2
  申请人：——

  公开号：US9163038B2

  公开（公告）日：2015-10-20
• Synthesis and positive inotropic effect of 1-alkyl- and 1-acyl-6,7-dimethoxy-3-dimethylamino-1,2,3,4-tetrahydroquinolines
  作者：F SANTANGELO、C CASAGRANDE、G MIRAGOLI、V VECCHIETTI

  DOI：10.1016/0223-5234(94)90110-4

  日期：——

  In the search for new positive inotropic agents we have investigated a series of 3-dimethylamino-1,2,3,4-tetrahydroquinolines with various substituents on the nitrogen of the quinoline ring. The N-isobutyryl derivative 20 (S903) was selected as the most interesting compound. Interestingly, while cardiac contractility was increased in vitro, heart rate was unchanged or slightly decreased. The positive inotropic activity was partly dependent on an indirect sympathomimetic effect. The (S) absolute configuration of the (-)enantiomer of S903 was established by correlation with (S)-L-dopa.