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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 11
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Original Articles

Synthesis of New Tandospirone Analogues Carrying 1-(3-(Trifluoromethyl)phenyl)piperazine

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Pages 1619-1628 | Received 11 Oct 2013, Published online: 14 May 2014

REFERENCES

  • (a) Kulig , K. ; Sapa , J. ; Nowaczyk , A. ; Filipek , B. ; Malawska , B. Design, synthesis, and pharmacological evaluation of new 1-[3-(4-arylpiperazin-1-yl)-2-hydroxy-propyl]-3,3-diphenylpyrrolidin-2-one derivatives with antiarrhythmic, antihypertensive, and alpha-adrenolytic activity . Eur. J. Med. Chem. 2009 , 44 , 3994 – 4003 ; (b) Sarswat , A. ; Kumar , R. ; Kumar , L. ; Lal , N. ; Sharma , S. ; Prabhakar , Y. S. ; Pandey , S. K. ; Lal , J. ; Verma , V. ; Jain , A. ; Maikhuri , J. P. ; Dalela , D. ; Gupta , G. ; Sharma , V. L. Arylpiperazines for management of benign prostatic hyperplasia: Design, synthesis, quantitative structure–activity relationships, and pharmacokinetic studies . Eur. J. Med. Chem. 2011 , 54 , 302 – 311 .
  • (a) Przegaliński , E. ; Baran , L. ; Siwanowicz , J. Role of 5-hydroxytryptamine receptor subtypes in the 1-[3-(trifluoromethyl)phenyl] piperazine-induced increase in threshold for maximal electroconvulsions in mice. Epilepsia 1994, 35, 889–894; (b) Pickard , G. E. ; Rea , M. A. TFMPP, a 5HT1B receptor agonist, inhibits light-induced phase shifts of the circadian activity rhythm and c-Fos expression in the mouse suprachiasmatic nucleus. Neuroscience Lett. 1997, 231, 95–98.
  • (a) Kishimoto , K. ; Koyama , S. ; Akaike , N. Presynaptic modulation of synaptic gamma-aminobutyric acid transmission by tandospirone in rat basolateral amygdala . Eur. J. Pharmacol. 2000 , 407 , 257 – 265 ; (b) Amano , T. ; Akbar , M. ; Matsubayashi , H. ; Sasa , M. Inhibitory effects of tandospirone, a 5-HT1A agonist, on medial vestibular nucleus neurons responding to lateral roll tilt stimulation in rats . Brain Research 2001 , 910 , 195 – 198 ; (c) Nishikawa , H. ; Inoue , T. ; Izumi , T. ; Koyama , T. Synergistic effects of tandospirone and selective serotonin reuptake inhibitors on the contextual conditioned fear stress response in rats . Eur. Neuropsychopharmacol. 2007 , 17 , 643 – 650 ; (d) Takahashi , T. ; Mitsuya , H. ; Murata , T. ; Murayama , J. ; Wada , Y. Opposite effects of SSRIs and tandospirone in the treatment of REM sleep behavior disorder . Sleep Medicine 2008 , 9 , 317 – 319 .
  • (a) Kossakowski , J. ; Jarocka , M. Synthesis of new N-substituted cyclic imides with an expected anxiolytic activity, XVII: Derivatives of 1-ethoxybicyclo[2.2.2]-oct-5-one-2,3-dicarboximide . Farmaco 2001 , 56 , 785 – 789 ; (b) Kossakowski , J. ; Bielenica , A. ; Mirosław , B. ; Koziol , A. E. ; Dybala , I. ; Struga , M. 4-Azatricyclo[5.2.2.02,6]undecane-3,5,8-triones as potential pharmacological agents . Molecules 2008 , 13 , 1570 – 1583 ; (c) Makan , S. Y. ; Tsymbal , D. I. ; Soboleva , S. G. ; Tarabara , I. N. ; Kas'yan , L. I. ; Andronati , S. A. N-[4-(arylpiperazin-1-yl)butyl]bicyclo[2.2.1]hept-5-ene-endo-2, endo-3-dicarboximides and their epoxy derivatives: Synthesis and affinity for 5HT1a receptors . Russian J. General Chem. 2009 , 79 , 292 – 296 .
  • Kulu , I. ; Kopruceli , A. ; Goksu , G. ; Ocal , N. Synthesis of new aryl(hetaryl)-substituted tandospirones under reductive Heck-type hydroarylations and isoxazoline derivatives via 1,3-dipolar cycloaddition reactions with expected anxiolytic activity . Curr. Org. Synth. 2013 , 10 , 481 – 485 .
  • (a) Kulu , I. ; Goksu , G. ; Sucu , B. O. ; Kopruceli , A. ; Ocal , N. ; Kaufmann , D. E. Synthesis of new aryl-substituted tandospirone and epiboxidine analogues and isoxazoline derivatives . Org. Prep. Proced. Int. 2013 , 45 , 44 – 56 ; (b) Gunkara , O. T. ; Sucu , B. O. ; Ocal , N. Synthesis of new aryl(hetaryl)-substituted tandospirone analogues with potential anxiolytic activity via reductive Heck-type hydroarylations . Chem. Papers 2013 , 67 , 643 – 649 .
  • (a) Namyslo , J. C. ; Kaufmann , D. E. Chemistry in the ambient field of the alkaloid epibatidine, 2: Triphenylarsine as an efficient ligand in the Pd-catalyzed synthesis of epibatidine and analogs . Synlett 1999 , 1999 , 114 – 116 ; (b) Namyslo , J. C. ; Storsberg , J. ; Klinge , J. ; Gärtner , C. ; Yao , M. L. ; Ocal , N. ; Kaufmann , D. E. The hydroarylation reaction: Scope and limitations . Molecules 2010 , 15 , 3402 – 3410 .
  • (a) Yolacan , C. ; Bagdatli , E. ; Ocal , N. ; Kaufmann , D. E. Epibatidine alkaloid chemistry, 5: Domino-Heck reactions of azabicyclic and tricyclic systems . Molecules 2006 , 11 , 603 – 614 ; (b) Bagdatli , E. ; Ocal , N. ; Kaufmann , D. E. An investigation into domino-Heck reactions of N-acylamino-substituted tricyclic imides: Synthesis of new prospective pharmaceuticals . Helv. Chim. Acta 2007 , 90 , 2380 – 2385 ; (c) Goksu , G. ; Gul , M. ; Ocal , N. ; Kaufmann , D. E. Hydroarylation of bicyclic, unsaturated dicarboximides: Access to aryl-substituted, bridged perhydroisoindoles . Tetrahedron Lett. 2008 , 49 , 2685 – 2688 ; (d) Goksu , G. ; Ocal , N. ; Kaufmann , D. E. Reductive Heck reactions of N-methyl-substituted tricyclic imides . Molecules 2010 , 15 , 1302 – 1308 .
  • (a) Celik , C. ; Kulu , I. ; Ocal , N. ; Kaufmann , D. E. Domino-Heck reactions of carba- and oxabicyclic, unsaturated dicarboximides: Synthesis of aryl-substituted, bridged perhydroisoindole derivatives . Helv. Chim. Acta 2009 , 92 , 1092 – 1101 ; (b) Kulu , I. ; Ocal , N. The synthesis of epiboxidine and related analogs as potential pharmacological agents . Helv. Chim. Acta 2011 , 94 , 2054 – 2060 .
  • Gul , M. ; Kulu , I. ; Gunkara , O. T. ; Ocal , N. Reductive Heck reactions and [3+2] cycloadditions of unsaturated N,N′-bistricyclic imides. Acta Chim. Slov. 2013, 60, 87–94.
  • Tindale , J. J. ; Hartlen , K. D. ; Alizadeh , A. ; Workentin , M. S. ; Ragogna , P. J. Maleimide-modified phosphonium ionic liquids: A template towards (multi)task-specific ionic liquids . Chem. Eur. J. 2010 , 16 , 9068 .
  • Ishihara , Y. ; Bazzi , H. S. ; Toader , V. ; Godin , F. ; Sleiman , H. F. Molecule-responsive block copolymer micelles . Chem. Eur. J. 2007 , 13 , 4560 – 4570 .
  • Badio , B. ; Garraffo , H. M. ; Plummer , C. V. ; Padgett , L. W. ; Daly , J. W. Synthesis and nicotinic activity of epiboxidine: An isoxazole analogue of epibatidine . Eur. J. Pharmacol. 1997 , 321 , 189 – 194 .
  • Peksel , A. ; Celik , C. ; Ocal , N. ; Yanardag , R. Antioxidant and radical scavenging activities of some norcantharidin and bridged perhydroisoindole derivatives . J. Serb. Chem. Soc. 2013 , 78 , 15 – 25 .

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