exo-(2R,4aS,5R,10bS)-5-phenyl-9-trifluoromethyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-2-ylmethylamine

• 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: exo-(2R,4aS,5R,10bS)-5-phenyl-9-trifluoromethyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-2-ylmethylamine
• 英文别名: ((2R,4aS,5R,10bS)-5-phenyl-9-(trifluoromethyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-2-yl)methanamine；[(2R,4aS,5R,10bS)-5-phenyl-9-(trifluoromethyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-2-yl]methanamine
• 化学式: C₂₀H₂₁F₃N₂O
• 分子量: 362.395
• InChiKey: CJHMDTGGICGPNW-PDWMJMLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  exo-(2R,4aS,5R,10bS)-5-phenyl-9-trifluoromethyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-2-ylmethylamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到N-[[(2R,4aS,5R,10bS)-5-phenyl-9-(trifluoromethyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-2-yl]methyl]ethenesulfonamide
  参考文献：
  名称：

  Substituted Tetrahydroquinolines

  摘要：

  本发明揭示了式(I)的化合物，其中W、R、R1、R2、R3、R4、R5、R6和R7具有权利要求书中所示的含义。该化合物可用于肿瘤治疗等方面。

  公开号：

  US20080194615A1
• 作为产物：
  描述：

  [(2R,4aS,5R,10bS)-5-phenyl-9-(trifluoromethyl)-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-2-yl]methyl methanesulfonate 在 氨 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以98%的产率得到exo-(2R,4aS,5R,10bS)-5-phenyl-9-trifluoromethyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinolin-2-ylmethylamine
  参考文献：
  名称：

  Substituted Tetrahydroquinolines

  摘要：

  本发明揭示了式(I)的化合物，其中W、R、R1、R2、R3、R4、R5、R6和R7具有权利要求书中所示的含义。该化合物可用于肿瘤治疗等方面。

  公开号：

  US20080194615A1

文献信息

• SUBSTITUTED TETRAHYDROQUINOLINES
  申请人：Schiemann Kai

  公开号：US20100022579A1

  公开（公告）日：2010-01-28

  Compounds of the formula (I), in which R 1 , R 2 , R 3 , R 4 , R 5 , X, Y, W, Q 1 , Q 2 , Z, s and m have the meanings indicated in claim 1, can be employed, inter alia, for the treatment of tumours.

  化合物的结构式（I）中，其中R1、R2、R3、R4、R5、X、Y、W、Q1、Q2、Z、s和m具有权利要求书中指定的含义，可用于治疗肿瘤。
• PROCESS FOR PREPARING TETRAHYDROQUINOLINE DERIVATIVES
  申请人：Emde Ulrich

  公开号：US20100311976A1

  公开（公告）日：2010-12-09

  The invention relates to a novel process for preparing enantiomerically enriched or pure tetrahydroquinoline derivatives by reacting a chiral dihydropyran-methylamine C with a aldehyde B and an aniline A in a multicomponent one pot synthesis in the presence of a protonic acid or Lewis acid with a suitable solvent. A, B, C have the meaning as described in the specification.

  本发明涉及一种新型的工艺，通过在质子酸或路易斯酸的适当溶剂存在下，将手性二氢吡喃-甲基胺C与醛B和苯胺A在多组分一锅法合成中反应，制备对映体富集或纯的四氢喹啉衍生物。其中，A、B、C的含义如规范中所述。
• The discovery and optimization of hexahydro-2H-pyrano[3,2-c]quinolines (HHPQs) as potent and selective inhibitors of the mitotic kinesin-5
  作者：Kai Schiemann、Dirk Finsinger、Frank Zenke、Christiane Amendt、Thorsten Knöchel、David Bruge、Hans-Peter Buchstaller、Ulrich Emde、Wolfgang Stähle、Soheila Anzali

  DOI：10.1016/j.bmcl.2010.01.110

  日期：2010.3

  Here we describe the discovery and optimization of hexahydro-2H-pyrano[3,2-c]quinolines (HHPQs) as potent and selective inhibitors of the mitotic kinesin-5 originally found during a high-throughput screening (HTS) campaign sampling our in-house compound collection. The compounds optimized subsequently and characterized herein were potently inhibiting the ATPase activity of Kinesin-5 and also exhibited consistent cellular activity, in that cells arrested in mitosis and apoptosis induction could be observed. X-ray crystallographic data demonstrated that these inhibitors bind in an allosteric pocket of Kinesin-5 distant from the nucleotide and microtubule binding sites. The selected clinical candidate EMD 534085 caused strong growth inhibition in human tumor xenograft models using Colo 205 colon carcinoma cells at doses below 30 mg/kg administered twice weekly without showing severe toxicity as determined by loss of body weight. (C) 2010 Elsevier Ltd. All rights reserved.
• WO2007/147480
  申请人：——

  公开号：——

  公开（公告）日：——
• 2-(Hetero)-aryl substituted tetrahydrochinoline
  申请人：Schiemann Kai

  公开号：US20070203167A1

  公开（公告）日：2007-08-30

  Compounds of the formula I, in which W, R, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings indicated in Claim 1 , can be employed, inter alia, for the treatment of tumours