Abstract
A series of 5-aryltetrahydro-gamma-carbolines was prepared by a novel N-arylation procedure and tested for neuroleptic activity in a rat antiamphetamine model. The systematic exploration of structural parameters leading to 8-fluoro-5-(4-fluorophenyl)-2-[4-hydroxy-4-(4-fluorophenyl)butyl]-2,3,5-tetrahydro-1H-pyrido[4,3-b]indole (CP-36,584, flutroline), a potent and long-acting neuroleptic compound, is described. These semirigid compounds provide a new, structurally distinct series with which to probe the conformational requirements for potent activity at the dopamine receptor.
Citations
Dec 30, 2004·Angewandte Chemie·Michael C WillisIan P Holmes
Jan 1, 1983·Neuroscience and Biobehavioral Reviews·J N Joyce
Jun 30, 2012·Journal of Medicinal Chemistry·Alexander G DossetterMadeleine Vickers
Sep 17, 2011·Organic Letters·Yunmi LeeEric N Jacobsen
Nov 16, 2007·Chemical Communications : Chem Comm·Anthony J FletcherMichael C Willis
Jul 25, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Can ChenQinglin Jiang
Sep 23, 2014·European Journal of Medicinal Chemistry·Robert OttoChristoph Enzensperger
Nov 27, 2009·European Journal of Medicinal Chemistry·Alexandre V IvachtchenkoVolodymyr M Kysil
May 16, 2009·Bioorganic & Medicinal Chemistry Letters·Alexandre V IvachtchenkoSergey E Tkachenko
Sep 1, 1984·Biomedical Mass Spectrometry·F C FalknerF G Mullins
Oct 15, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Miao ShenWen-Hua Sun
Nov 19, 2009·Archiv der Pharmazie·Alexandre V IvachtchenkoSergey E Tkachenko
Dec 6, 2019·Nature Communications·Shi-Ming XuChun-Jiang Wang
Dec 1, 1993·Archiv der Pharmazie·J LehmannN Jiang
Feb 21, 2009·Chemistry : a European Journal·Yi-Fei ShengShu-Li You
Feb 16, 2013·Organic & Biomolecular Chemistry·Jinglei LvKang Zhao
Jan 12, 2021·Organic Letters·Fan XiaoChun-Jiang Wang
Sep 19, 2020·Journal of Medicinal Chemistry·Nicoletta BrindaniFabio Bertozzi
Mar 16, 2021·The Journal of Organic Chemistry·Souvik GuhaSubhabrata Sen
Jan 2, 2008·The Journal of Physical Chemistry. a·Pei-Yi WangYan-Rong Li
Sep 26, 2002·Journal of the American Chemical Society·Jon C AntillaStephen L Buchwald
Jul 6, 2021·Beilstein Journal of Organic Chemistry·Premansh DudheVenkatesh Chelvam
Oct 4, 2002·Journal of Medicinal Chemistry·Battistina AsproniGiovanni Biggio
Aug 17, 2004·The Journal of Organic Chemistry·Jon C AntillaStephen L Buchwald
Feb 14, 2006·The Journal of Organic Chemistry·Olga Soares do Rêgo BarrosGilson Zeni